Cycloimido-substituted benzofused heterocyclic herbicides

ABSTRACT

Novel herbicidal compounds, compositions containing them, and methods for their use in controlling weeds are disclosed. The novel herbicidal compounds are represented by formula I: ##STR1## where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached at the 7 position of a benzofuran, benzoxazole, indole, 2,3-dihydrobenzimidazole or benzimidazole, and X is selected from hydrogen, halogen, cyano, nitro, and amino. Preferred R groups are optionally substituted alkyl groups.

This application claims the benefit of U.S. Provisional Application No.60/039,172 filed Feb. 26, 1997.

BACKGROUND OF THE INVENTION

The present invention relates generally to novel herbicidal compoundsand methods for their use in controlling unwanted plant species inagriculture. In particular, the present invention pertains tocycloimido-substituted benzofused heterocyclic herbicides, and moreparticularly it pertains to herbicides in which the benzofusedheterocycle is a benzofuran, benzimidazole, a 2,3-dihydrobenzimidazole,or indole having a cycloimido moiety which is a1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a3,4,5,6-tetrahydrophthalimid-1-yl, a4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl,or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring.

SUMMARY OF THE INVENTION

It has now been found that certain cycloimido-substituted benzofusedheterocyclic compounds are useful as pre-emergent and postemergentherbicides. These novel compounds are represented by formula I: ##STR2##where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a3,4,5,6-tetrahydrophthalimid-1-yl, a4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl,or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached atthe 7 position of a benzofuran, benzoxazole, 2,3-dihydrobenzimidazole,indole or benzimidazole, and X is selected from hydrogen, halogen,cyano, nitro, alkyl, haloalkyl, and amino. Preferred R groups areoptionally substituted alkyl groups.

DETAILED DESCRIPTION OF THE INVENTION

Certain cycloimido-substituted benzofused heterocyclic compounds havenow been found to be useful as pre- and postemergent herbicides. Thesecompounds are represented by formula I: ##STR3## where (1) A is nitrogendouble-bonded to position 2 and B is oxygen;

(2) A is oxygen and B is CR¹ double bonded to position 2;

(3) A is NH and B is nitrogen double-bonded to position 2;

(4) A is nitrogen double bonded to position 2 and B is NR² ;

(5) A is CH double bonded to position 2 and B is NR² ;

(6) A is NH and B is CR¹ double bonded to position 2; or

(7) A and B are NH

R is hydrogen, hydroxy, mercapto, straight or branched chain loweralkyl, cycloalkyl, alkoxy, aryl, heteroaryl, alkenyl, haloalkyl,hydroxyalkyl, haloaryl, alkoxyaryl, arylalkyl, aryloxyalkyl,haloarylalkyl, alkylthio, heterocyclyl, alkoxyalkyl,alkoxylalkyloxyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl,aminocarbonyloxyalkyl, aminoalkyl, cyanoalkyl, aminoalkenyl, carboxy,carboxyalkyl, alkylcarboxy, alkylcarboxyalkyl, formyl, aminocarbonyl,amino, oxygen, cyano, nitro, alkylsulfonyl, aminosulfonyl,alkylsulfonylamino, alkoxycarbonyloxyalkyl, alkylcarboxylalkoxy,alkoxycarbonylamino, alkoxycarbonylalkylaminoalkyl, aryliminoalkyl,(aryl)(alkoxy)alkyl, (aryl)(alkylcarbonyloxy)alkyl, arylalkoxyalkyl,cyanoalkylthio, alkynylalkylthio, arylalkylthio, cyanothio,cyanothioalkyl, alkoxycarbonylalkylthio, aminocarbonylalkylthio,alkenylalkylthio, haloalkylalkynylalkylthio, aminocarbonyloxyalkyl,arylalkylcarbonylaminoalkyl, (hydroxy)(aryl)alkyl,alkylcarbonylaminoalkyl, alkylsulfonylaminoalkyl, aminocarbonylalkyl,alkoxycarbonyl, and alkenyloxy, where the amino group may be substitutedwith one or two substituents independently selected from alkyl, hydroxy,alkoxy, carboxy, aryl, alkylsufonyl, or haloalkylsulfonyl;

R¹ is hydrogen, lower alkyl, or haloalkyl;

R² is hydrogen, alkyl, haloalkyl, CO₂ (alkyl), CH₂ CO₂ (alkyl), CH₂CONH--alkyl, CH₂ CON(alkyl)₂, CH₂ CO₂ H, CH₂ OCH₃, SO₂ (alkyl), CH₂CH═CH₂, CH₂ C.tbd.CH.

X is selected from hydrogen, F, Cl, Br, alkyl, haloalkyl, CN, NO₂, andNH₂ ;

n is 0-3;

J is selected from ##STR4## and R³ is selected from hydrogen, alkyl,haloalkyl, CH₂ CN, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ CO₂ (alkyl), CH₂ OCH₃,and NH₂.

Preferred compounds are those of formula I where R is CH₃, CH₂ CH₃,C(CH₃)₂ OH, CH₂ CH₂ OH, CH(CH₃)₂, t-butyl, CF₃, CH(F)CH₃, CF₂ CF₃,C(CH₃)₂ OCOCH₃, C(CH₃)₂ NHSO₂ CH₃, CH₂ CH₂ CH₂ C.tbd.N, CH₂ CH₂ CO₂ CH₃,and CON(CH₃)₂ ; X is a chlorine, bromine or fluorine substituted in oneor both of positions 4 and 6; J is ##STR5## and R³ is CH₃ or NH₂.

One aspect of the present invention relates to compounds of formula I inwhich A is nitrogen double-bonded to position 2 and B is oxygen, and R,R³, J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A is oxygen and B is CR¹ double bonded to position 2, and R,R¹, R³, J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A is NH and B is nitrogen double-bonded to position 2, and R,J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A is nitrogen double bonded to position 2 and B is NR²,and R,R², R³, J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A is CH double bonded to position 2 and B is NR², and R, R²,R³, J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A is NH and B is CR¹ double bonded to position 2, and R, R¹,R³, J, X and n are as described above.

Another aspect of the present invention relates to compounds of formulaI in which A and B are NH and R, R¹, R³, J, X and n are as describedabove.

Another aspect of the present invention relates to compounds of formulaI where J is not ##STR6## when: A is oxygen and B is CR¹ double bondedto position 2; A is CH double bonded to position 2 and B is NR² ; or Ais NH and B is CR¹ double bonded to position 2; and R, R¹, R³, X, and nare as described above.

As shown in the specification a wide range of substituents is describedfor position B in compounds of formula I whereas position A is generallyunsubstituted. It was found that some herbicidal activity is retainedwhen a methyl substituent is placed at position A, but that substitutionat that position generally causes a sharp decrease in activity.

Certain intermediates of the present invention are novel. These includecompounds of formula II: ##STR7## where Y is NO₂, NH₂, or --NHN═C(CH₃)R;Z is hydrogen, F, NH₂, or OH; and R, J, X, and n are as described above;with the proviso that when Y is --NHN═C(CH₃)R, Z is hydrogen.

As used in this specification and unless otherwise indicated, the terms"alkyl," "alkenyl," "alkynyl," "haloalkyl," and "alkoxy" used alone oras part of a larger moiety, includes straight or branched carbon chainsof 1 to 6 carbon atoms. "Halogen" refers to fluorine, bromine orchlorine. "THF" means tetrahydrofuran, "DMF" meansN,N-dimethylformamide, and "DBU" means1,8-diazabicyclo[5.4.0]undec-7-ene. When "n" in is 2 or 3, thesubstituents X may be the same or different from one another.

SCHEME 1 ##STR8## a) 70% HNO₃ /H₂ SO₄, 0-5° C.; (b) NaOSi(CH₃)₃, MeOH,dioxane; (c) Fe, EtOH, acetic acid, HCl, heat; (d) CF₃ C(NH₂)═CO₂ CH₂CH₅, NaOSi(CH₃)₃, DBU, DMF; (e) CH₃ I, K₂ CO₃, DMF, 60-80° C.; (f) HCl,NaNO₂, Nal, H₂ O; (g) BBr₃, CH₂ Cl₂ ; (h) HC.tbd.CR,Pd(Ph₃ P)₂ Cl₂, Cul,triethylamine.

Benzofurans of formula I, where A is oxygen and B is CH double bonded toposition 2, may be generally prepared as shown in Scheme 1. Startingwith an appropriately substituted fluoroaniline derivative 1, nitrationprovides intermediate 2. Displacement of the fluorine of 2 with amethoxy group as shown in step b, followed by reduction of the nitrogroup as shown in step c provide the methoxyaniline 3. Themethoxyaniline 3 is a versatile intermediate from which a number ofcompounds of the present invention can be made by attachment of variousJ groups. For example, a uracil ring may be appended as shown in step dto give intermediate 4a. At this point, R³ substituents other than H maybe introduced, as shown for example in step e to provide 4b where R³ ismethyl. Using diazotization conditions (step f) 4b is converted to theiodoanisole 5 which is then deprotected to give the iodophenol 6.Palladium-catalyzed acetylenic coupling and ring closure as shown instep h give benzofurans 7 of the present invention. To obtainbenzofurans of formula I where the J group is other than uracil,approaches analogous to that outlined in Scheme 1 may be followed. Suchapproaches based on Scheme 1 would be known to one skilled in the art.

Scheme 2 ##STR9## a) 70% HNO₃ /H₂ SO₄, 0-5° C.; (b) Fe, aqueous aceticacid, 50° C.; (c) RCOCl, pyridinium p-toluenesulfonate, triethylamine,xylene; (d) 1,1-carbonylimidazole, THF; (e) R'-halide, Ag₂ O, CH₂ Cl₂(to give 11 where R═R'O).

Benzoxazoles of formula I, where A is nitrogen double bonded to position2 and B is oxygen, may be prepared as shown in Scheme 2 above. Startingwith a phenol such as intermediate 8 nitration under standard conditionsgives the nitrophenol 9. Certain of the benzoxazoles 11 of the presentinvention may be obtained by reduction of 9 to the aniline 10 followedby treatment with an acid halide (such as shown in step c).Alternatively, other benzoxazoles 11 may be obtained by treating 10 withcarbonyldiimidazole to give intermediate 12 which can be O-alkyatedaccording to step e. The approach outlined in Scheme 2 can be adapted,in ways known to one skilled in the art, to obtain benzoxazoles offormula I where the J group is other than uracil.

Scheme 3 ##STR10## a) see steps (d) and (e) of Scheme 1; (b) 70% HNO₃/H₂ SO₄, 0-5° C.; (c) NH₄ OAc, triethylamine, dioxane, heat; (d) SnCl₂H₂ O or Fe, NH₄ Cl, aqueous ethanol, heat; (e) RCO₂ H, heat; RCO-halide,CH₂ Cl₂ /Pyridine, then POCl₃, CH₂ Cl₂ ; alkoxycarbonyl isothiocyanate,HgCl₂, heat (where R is --NHCO₂ alkyl); or thiophosgene, EtOAC, heat(where R is --SH).

Benzimidazoles of formula I, where A is NH and B is nitrogen doublebonded to position 2, may be prepared as shown in Scheme 3 above. Forexample, intermediate 13 may be converted to the uracil 14 by thewell-known chemistry previously described. Nitration of 14 followed byaminolysis of the fluorine group (steps b and c) provides thenitroaniline 15. The diamine 16 is obtained by reduction of 15 understandard conditions. Benzimidazoles 17 of the present invention areobtained by treatment of 16 with a carboxylic acid, an acid halide, analkoxycarbonyl isothiocyanate, or thiophosgene according to step e.Other benzimidazoles 17 of the present invention are obtained byderivativization of benzimidazoles depicted in Scheme 3 using techniquesknown to one skilled in the art. The approach outlined in Scheme 3 canbe adapted, in ways known also to one skilled in the art, to obtainbenzimidazoles of formula I where the J group is other than uracil.##STR11##

Benzimidazoles of structure 17A where R³ is NH₂ are prepared in a manneranalogous to that depicted in Scheme 3, except the NH₂ group is attachedfollowing nitration of the phenyl ring. The 1-unsubstituted uracil ringis formed as previously described in step d of Scheme 1, followed bynitration of the phenyl ring (Scheme 3, step b). The uracil ring is thenaminated in the 1-position by methods known in the art by treating itwith 1-aminooxysulfonyl-2,4,6-trimethylbenzene. The 1-aminouracil isthen subjected to aminolysis of the phenyl fluorine (step c) followed byreduction to the diamine (step d). ##STR12##

2,3-Benzimidazoles of formula I, where A and B are NH may be preparedfrom Intermediate 16 in Scheme 3 by heating it with an appropriatelysubstituted acetaldehyde ethyl hemiacetal, affording compounds ofStructure 17B.

Scheme 4 ##STR13##

a) i. NaNO₂, HCl; ii. SnCl₂ 2H₂ O; iii. RCOCH₃ ; (b) polyphosphoricacid, 80° C.

Indoles of formula I, where A is CH double bonded to position 2 and B isNR¹, may be prepared according to Scheme 4 above. Using a Fischer indoleroute the starting aniline 18 may be converted to the correspondinghydrazone 19 which in turn may be cyclized under acidic conditions suchas is shown in step b. The resulting indoles 20 of the present inventionmay be further derivatized by alkylation of the indole ring nitrogen toindoles of formula I where R¹ is other than hydrogen. The approachoutlined in Scheme 4 can be adapted, in ways known to one skilled in theart, to obtain indoles of formula I where the J group is other thanuracil. ##STR14##

Indoles of formula I, where A is NH and B is CR¹ double bonded toposition 2, may be prepared by a Fischer indole synthesis analogous tothat shown in Scheme 4 starting with aniline 21. Substitution at the 3position of indoles such as 22 with R¹ groups is known to one skilled inthe art.

Compounds of the present invention may also be prepared in accordancewith the procedures shown in the Examples below, by procedures analogousto those shown in the Examples, or by other methods that are generallyknown or available to one skilled in the art.

EXAMPLE 11-Methyl-6-Trifluoromethyl-3-[7-Bromo-5-Fluoro-2-(2-Methylcarbonyloxyprop-2-yl)Benzoxazol-4-yl]-2,4(1H,3H)-Pyrimidinedione(Compound 104)

Step A1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione

A stirred solution of 17.0 grams (0.044 mole) of1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneand 5.0 grams (0.050 mole) of sulfuric acid in 100 mL of glacial aceticacid was cooled to 15° C., and 3.2 grams (0.050 mole) of 70% nitric acidwas added dropwise. The reaction mixture was then allowed to warm toambient temperature where it stirred for two hours. The reaction mixturewas poured into water and extracted with diethyl ether. The extract wasconcentrated under reduced pressure to a residue. The residue waspurified by column chromatography on silica gel, yielding 16.4 grams oftitle compound; mp 76-78° C.

Step B1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

A stirred solution of 16.0 grams (0.037 mole) of1-methyl-6-trifluoromethyl-3-(4-bromo-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedioneand 10 mL of water in 120 mL of glacial acetic acid was heated to 50°C., and 16.0 grams (excess) of iron dust was slowly added. The reactionmixture was then cooled to ambient temperature where it stirred for onehour. The reaction mixture was filtered through diatomaceous earth, andthe filtrate was partitioned in a mixture of 150 mL portions each ofwater and ethyl acetate. The organic layer was separated, dried withmagnesium sulfate, and filtered. The filtrate was concentrated underreduced pressure to a residue. The residue was purified by columnchromatography on silica gel, yielding 12.0 grams of title compound; mp98-100° C.

Step C Compound 104

A stirred solution of 0.50 gram (0.0013 mole) of1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione,0.21 gram (0.0013 mole) of 1-chlorocarbonyl-1-methylethyl acetate, 0.14gram (0.0014 mole) of triethylamine, and 0.16 gram (0.0006 mole) ofpyridinium p-toluenesulfonate in 50 mL of xylene was heated at 150 ° C.for about 18 hours. The reaction mixture was then cooled to ambienttemperature and taken up in ethyl acetate. The solution was washed withwater and an aqueous solution saturated with sodium chloride; then itwas dried with magnesium sulfate. The mixture was filtered, and thefiltrate was concentrated under reduced pressure to a residue. Theresidue was purified by column chromatography on silica gel, yielding0.72 gram of Compound 104. The NMR spectrum was consistent with theproposed structure.

EXAMPLE 21-Methyl-6-Trifluoromethyl-3-(7-Bromo-5-Fluoro-2-Methoxy-Benzoxazol-4-yl-2,4(1H,3H)-Pyrimidinedione(Compound 109)

Step A1-methyl-6-trifluoromethyl-3-(7-bromo-5-fluorobenzoxazol-2-on-4-yl)-2,4(1H,3H)-pyrimidinedione

A stirred solution of 2.0 grams (0.005 mole) of1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneand 1.2 grams (0.008 mole) of carbonylimidazole in 50 mL of THF washeated at reflux for three hours. The reaction mixture was cooled andconcentrated under reduced pressure to a residue. The residue waspurified by column chromatography on silica gel, yielding 1.1 grams oftitle compound. The NMR spectrum was consistent with the proposedstructure.

Step B Compound 109

A mixture of 0.50 gram (0.001 mole) of1-methyl-6-trifluoromethyl-3-(7-bromo-5-fluorobenzoxazol-2-on-4-yl)-2,4(1H,3H)-pyrimidinedione0.17 gram (0.001 mole) of methyl iodode, and 0.27 gram (0.001 mole) ofsilver(l) oxide in 50 mL of methylene chloride was stirred at ambienttemperature for two hours. The product was isolated from the reactionmixture by column chromatography on silica gel, yielding 0.28 gram ofCompound 109. The NMR spectrum was consistent with the proposedstructure.

EXAMPLE 31-Methyl-6-Trifluoromethyl-3-[7-Chloro-5-Fluoro-2-(1-Methylethyl)Benzoxazol-4-yl]-2,4(1H,3H)-Pyrimidinedione(Compound 28)

Step A1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

A stirred solution of 18.2 grams (0.054 mole) of1-methyl-6-trifluoromethyl-3-(5-amino-4-chloro-2-fluorophenyl)-2,4(1H,3H)-pyrimidinedionein 100 mL of sulfuric acid was cooled to 5° C., and a solution of 3.7grams (0.054 mole) of sodium nitrite in about 10 mL of water was addeddropwise. The reaction mixture was then warmed to ambient temperaturewhere it stirred for two hours. In a separate reaction vessel, a stirredmixture of 242 grams (0.970 mole) of copper(II) sulfate and 1.5 grams(0.005 mole) of iron(II) sulfate heptahydrate in about 300 mL of waterand 300 mL of xylene was heated to reflux, and the pyrimidinedionediazonium solution prepared above was added dropwise. The reactionmixture was stirred at reflux for two additional hours, then allowed tocool as it stirred for about 18 hours. The reaction mixture was pouredinto about 600 mL of water, and the aqueous/organic layers wereseparated. The aqueous layer was washed with ethyl acetate, and the washwas combined with the organic layer. The combined organic material waswashed with water, then with an aqueous solution saturated with sodiumchloride. The organic material was dried with magnesium sulfate andfiltered. The filtrate was concentrated under reduced pressure, yieldingimpure product. The product was dissolved in diethyl ether and washedwith aqueous 10% hydrochloric acid, and with water. The diethyl ethersolution was dried with magnesium sulfate and filtered. The filtrate wasconcentrated under reduced pressure, yielding 7.6 grams of titlecompound. The NMR spectrum was consistent with the proposed structure.

Step B1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione

This compound was prepared in the manner of Step A of Example 1, using3.8 grams (0.011 mole) of1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione,1.0 gram (0.011 mole) of 70% nitric acid, and 50 mL of sulfuric acid,yielding 1.5 grams of title compound. The NMR spectrum was consistentwith the proposed structure.

Step C1-methyl-6-trifluoromethyl-3-(6-amino-4-chloro-2-fluoro-5-hydroxy-phenyl)-2,4(1H,3H)-pyrimidinedione

This compound was prepared in the manner of Step B of Example 1, using1.5 grams (0.004 mole)1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione,3.0 grams (0.054 mole) of iron dust, and 5 mL of water in 50 mL ofglacial acetic acid, yielding 1.0 gram of title compound. The NMRspectrum was consistent with the proposed structure.

Step D Compound 28

This compound was prepared in the manner of Step C of Example 1, using0.52 gram (0.0015 mole) of1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione,0.18 gram (0.0017 mole) of isobutyryl chloride, 0.24 gram (0.0017 mole)of triethylamine, and 0.09 gram (0.0004 mole) of pyridiniump-toluenesulfonate in 50 mL of xylene, yielding 0.22 gram of Compound28. The NMR spectrum was consistent with the proposed structure.

EXAMPLE 4 Synthesis of3-(4-Chloro-6-Fluoro-2-Phenylbenzofuran-7-yl)-1-Methyl-6-Trifluoromethyl-2,4(1H,3H)-Pyrimidinedione(Compound 280)

Step A ethyl N-(4-chloro-2,6-difluoro-3-nitrophenyl)carbamate

A stirred solution of 23.6 grams (0.109 mole) of ethylN-(4-chloro-2,6-difluorophenyl)carbamate in 125 mL of concentratedsulfuric acid was cooled to about 0° C. and 7.7 mL (0.123 mole) of 70%nitric acid was added dropwise at a rate to maintain the reactiontemperature below 10° C. Upon completion of addition, the reactionmixture was stirred at 10° C. for 30 minutes and then allowed to warm toambient temperature where it stirred for about 18 hours. At theconclusion of this period, the reaction mixture was poured into 150 mLof ice-water. The resulting precipitate was collected by vacuumfiltration and washed with water followed by petroleum ether. Theprecipitate was dried in a heated vacuum desicator, yielding 30.6 gramsof title compound. The NMR spectrum was consistent with the proposedstructure.

Step B ethyl N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)carbamate

Under a nitrogen atmosphere, a solution of 30.6 grams (0.109 mole) ofethyl N-(4-chloro-2,6-difluoro-3-nitrophenyl)carbamate and 18 mL (0.449mole) of methanol in 175 mL of dioxane was stirred and 218 mL (0.218mole) of 1 M sodium trimethylsilanoate (in tetrahydrofuran) was addeddropwise during a 45 minute period. Upon completion of addition, thereaction mixture was heated to 65° C. where it stirred for three hours.At the conclusion of this period, the reaction mixture was allowed tocool to ambient temperature where it stirred for about 18 hours. Thereaction mixture was concentrated under reduced pressure to a residue.The residue was taken up in cold 3 N hydrochloric acid. The resultingsolid was collected by filtration, washed with petroleum ether, and heatdried under vacuum, yielding 21.3 grams of title compound. The NMRspectrum was consistent with the proposed structure.

Step C ethyl N-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)carbamate

Under a nitrogen atmosphere, a stirred solution of 21.3 grams (0.072mole) of ethyl N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)carbamate,18.3 grams (0.328 mole) of iron powder, 50 mL of acetic acid, and 250 mLof ethanol was heated to 65° C. where it stirred for two hours. At theconclusion of this time, 3 mL (0.036 mole) of 12 M hydrochloric acid wasadded. Upon completion of addition, the reaction mixture was stirred foran additional two hours. After this time, the reaction mixture wasconcentrated under reduced pressure to yield a brown oil. The oil wasthen taken up in methylene chloride. The mixture was filtered throughdiatomaceous earth, and the filter cake was washed with water and anaqueous saturated sodium bicarbonate solution. The filtrate was storedover sodium sulfate for about 18 hours and then filtered. The solventwas removed under reduced pressure to yield a black oil. This oil wasfiltered through a silica gel pad, yielding 15.0 grams of ethylN-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)carbamate. The NMR spectrumwas consistent with the proposed structure.

Step D3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

This compound was prepared using 4.0 grams (0.036 mole) of sodiumtrimethylsilanolate, 6.6 grams (0.036 mole) of ethyl3-amino-4,4,4-trifluorocrotonate, 8.5 grams (0.032 mole) of ethylN-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)carbamate, and 2.2 grams(0.014 mole) of DBU in 75 mL of DMF. This preparation differs fromwell-known literature preparations for pyrimidinedione rings in thatsodium trimethylsilanolate and DBU were used rather than sodium hydride.The yield of title compound was 1.7 grams. The NMR spectrum wasconsistent with the proposed structure.

Step E3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A solution of 7.5 grams (0.021 mole) of3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione,3.4 grams (0.025 mole) of potassium carbonate, and 3.5 grams (0.025mole) of methyl iodide in 200 mL of acetone was stirred at ambienttemperature for about 18 hours. The reaction mixture was thenconcentrated under reduced pressure, and the residue was taken up in 200mL of water. The mixture was extracted with two 100 mL portions of ethylacetate. The combined extracts were washed with two 50 mL portions of anaqueous saturated sodium chloride solution. The organic layer was driedwith magnesium sulfate, filtered, and concentrated under reducedpressure, yielding 6.9 grams of crude product. The dark oil was combinedwith 7.0 grams of crude product prepared by a similar route to yield atotal of 13.9 grams of crude product. The crude product was purified bycolumn chromatography on silica gel, yielding 10.0 grams of titlecompound. The NMR spectrum was consistent with the proposed structure.

Step F3-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A solution of 4.0 grams (0.011 mole) of3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedionein 25 mL (0.300 mole) of concentrated hydrochloric acid was stirred andcooled in an ice bath. During a 15 minute period, 1.9 grams (0.013 mole)of sodium nitrite was added dropwise at a rate to maintain the reactiontemperature at 15° C. Upon completion of addition, the mixture wasstirred for 20 minutes and then poured into 15.0 grams (0.090 mole) ofpotassium iodide. The reaction mixture was stirred for 30 minutes andthen filtered. The filter cake was thoroughly washed with distilledwater and then taken up in 150 mL of ethyl acetate. The resultingsolution was dried with sodium sulfate and filtered. The filtrate wasconcentrated under reduced pressure to yield a brown solid. The solidwas subjected to column chromatography on silica gel. Elution wasaccomplished using 5:1 heptane and ethyl acetate. The product-containingfractions were combined and concentrated under reduced pressure,yielding 3.0 grams of title compound. The NMR spectrum was consistentwith the proposed structure.

Step G3-(4-chloro-6-fluoro-2-hydroxy-3-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Under a nitrogen atmosphere, a stirred solution of 3.0 grams (0.006mole) of3-(4-chloro-6-fluoro-3-iodo-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 75 mL of methylene chloride was cooled in a dryice/acetone bath and 22.0 mL (0.022 mole) of 1 M boron tribromide (inmethylene chloride) was added dropwise during a 20 minute period. Uponcompletion of addition, the reaction mixture was allowed to warm toambient temperature were it stirred for about one hour. At theconclusion of this period, the reaction mixture was poured into 200 mLof water and extracted with two 50 mL portions of methylene chloride.The combined extracts were washed with one 100 mL portion of an aqueoussaturated sodium chloride solution, dried with sodium sulfate, andfiltered. The filtrate was concentrated under reduced pressure, yielding2.6 grams of title compound. The NMR spectrum was consistent with theproposed structure.

Step H Compound 280

Under a nitrogen atmosphere, a solution of 1.5 grams (0.003 mole) of3-(4-chloro-6-fluoro-2-hydroxy-3-iodophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione,0.41 gram (0.004 mole) of phenylacetylene, and 0.71 gram (0.007 mole) oftriethylamine in 25 mL of DMF was stirred. To this was added 0.09 gram(0.00013 mole) of dichlorobis(triphenylphosphine)pallidium (II) and 0.05gram (0.00026 mole) of copper (I) iodide. Upon completion of addition,the reaction mixture was heated to 70° C. where it stirred for 2.5hours. After this time, the reaction mixture was cooled to ambienttemperature and then poured into 150 mL of an aqueous 10% ammoniumchloride solution. The resulting precipitate was collected by filtrationand washed with water. The precipitate was taken up in 120 mL of ethylacetate. The resulting solution was dried with sodium sulfate andfiltered. The filtrate was concentrated under reduced pressure to abrown solid. The solid was recrystallized using 1:1 chloroform andpetroleum ether, yielding 0.31 gram of Compound 280. The mother liquorwas concentrated to a residue. The residue was recrystallized usingpetroleum ether to yield an additional 0.21 gram of Compound 280, m.p.215-216° C. The NMR spectrum was consistent with the proposed structure.

EXAMPLE 5 Synthesis of3-(4-Chloro-6-Fluoro-2-Trifluoromethylbenzimidazol-7-yl)-1-Methyl-6-Trifluoromethyl-2,4(1H,3H)-Pyrimidinedione

(Compound 365)

A stirred solution of 3.0 grams (0.0085 mole) of3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionein 15.0 mL of trifluoroacetic acid was heated to 65° C. where it stirredfor one hour. At the conclusion of this period, the reaction mixture wasanalyzed by TLC, which indicated that the reaction was not complete. Thereaction mixture was stirred at 65° C. for an additional two hours.After this time, the reaction mixture was again analyzed by TLC, whichindicated that the reaction was complete. The reaction mixture wasallowed to cool to ambient temperature and then poured into 200 mL ofwater. The resulting mixture was allowed to stand at ambient temperaturefor about 18 hours. At the conclusion of this period, the resultingsolid was collected by filtration and washed with water followed byheptane. The filter cake was dried under vacuum, yielding 3.6 grams ofCompound 365, m.p. 130° C. The NMR spectrum was consistent with theproposed structure.

EXAMPLE 6 Synthesis of3-(4-Chloro-2-Ethyl-6-Fluorobenzimidazol-7-yl)-1-Methyl-6-Trifluoromethyl-2,4(1H,3H)-Pyrimidinedione

(Compound 367)

Step A3-(4-chloro-2,6-difluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

Under a nitrogen atmosphere, a solution of 32.0 grams (0.900 mole) ofsodium hydride (60% by weight) in 250 mL of DMF was vigorously stirredand cooled in an ice bath. To this a solution of 133.0 grams (0.726mole) of ethyl 3-amino-4,4,4-trifluorocrotonate in 150 mL of DMF wasadded dropwise at a rate to maintain the reaction mixture temperature atabout 5° C. Upon completion of addition, a solution of 156.3 grams(0.663 mole) of ethyl N-(4-chloro-2,6-difluorophenyl)carbamate in 250 mLof DMF was added dropwise. Upon completion of addition, the mixture wasremoved from the ice bath and heated to 130° C. where it stirred for 3.5hours. After this time, the mixture was analyzed by gas chromatography(GC), which indicated that only a slight amount of the starting materialwas left. The mixture was cooled to 5° C. and 83.0 mL (1.333 moles) ofmethyl iodide was added dropwise at a rate to maintain the reactionmixture temperature below 20° C. Upon completion of addition, thereaction mixture was allowed to warm to ambient temperature where itstirred for about 18 hours. At the conclusion of this period, thereaction mixture was filtered through diatomaceous earth. The filtratewas concentrated under reduced pressure to yield a dark viscous oil. Theoil was taken up in methylene chloride and washed with three 1000 mLportions of water followed by one 1000 mL portion of an aqueoussaturated sodium chloride solution. The organic layer was dried withmagnesium sulfate, filtered, and concentrated under reduced pressure,yielding 223.8 grams of title compound. The NMR spectrum was consistentwith the proposed structure.

Step B3-(4-chloro-2,6-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A stirred solution of 211.0 grams (0.619 mole) of3-(4-chloro-2,6-difluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionein 600 mL of concentrated sulfuric acid was cooled to less than 10° C.,and 44 mL (0.689 mole) of aqueous 70% nitric acid was added dropwise ata rate to maintain the reaction temperature below 10° C. Upon completionof addition, the reaction mixture was analyzed by GC, which indicatedthe reaction was incomplete. The reaction was allowed to warm to ambienttemperature and an additional 5 mL (0.078 mole) of aqueous 70% nitricacid was added. The reaction mixture was again analyzed by GC, whichindicated the reaction was complete. The reaction mixture was pouredinto ice-water. The resulting solid was collected by filtration, washedwith water, and then taken up in 600 mL of methylene chloride. Theresulting solution was washed with two 600 mL portions of water, one 600mL portion of an aqueous saturated sodium bicarbonate solution, and one600 mL portion of an aqueous saturated sodium chloride solution. Theorganic layer was separated, dried with magnesium sulfate, and filtered.The filtrate was concentrated under reduced pressure, yielding a waxytan solid. The solid was triturated with heptane and allowed to standfor about 72 hours. At the conclusion of this period, the solid wascollected by filtration, washed with heptane, and dried under reducedpressure, yielding 201.4 grams of title compound. The NMR spectrum wasconsistent with the proposed structure.

Step C3-(6-amino4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

To stirred solution of 200 grams (0.519 mole) of3-(4-chloro-2,6-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionein 1000 mL of dioxane was added 150 mL (1.091 moles) of triethylamine inone portion. Upon completion of addition, the mixture was vigorouslystirred and 400 grams (5.189 moles) of ammonium acetate was added in oneportion. The reaction mixture was heated to 90° C. where it stirred fortwo hours. The reaction mixture was allowed to cool to ambienttemperature where it stirred for about 18 hours. The resultingsuspension was collected by filtration and washed with dioxane. Thefiltrate was concentrated under reduced pressure to yield a viscous darkoil. The oil was poured into ice-water. The resulting solid wascollected by filtration and washed with water. The solid was dried underreduced pressure and then at ambient temperature for about 18 hours,yielding 195.1 grams of title compound. The NMR spectrum was consistentwith the proposed structure.

Step D3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedioneand3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A solution of 278.0 grams (1.232.moles) of tin(II) chloride dihydrate,264.0 grams (4.936 moles) of ammonium chloride, 400 mL of water. and 800mL of ethanol was vigorously stirred, and 157.4 grams (0.411 mole) of3-(6-amino-4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionewas added. Upon completion of addition, the reaction mixture was heatedto 83-85° C. where it stirred for 18 hours. After this time the reactionmixture was allowed to cool to ambient temperature. The resultant solidby-product was collected by filtration and washed with ethanol. Thecombined filtrate and wash was concentrated under reduced pressure toyield a suspension of additional by-product. The suspension was taken upin ethyl acetate and the resultant emulsion was filtered through a padof diatomaceous earth. The filter cake was washed with ethyl acetate,and the combined organics were washed with three 200 mL portions ofwater. The organic layer was dried with magnesium sulfate, filtered, andconcentrated under reduced pressure to a brown residue. The residue wastriturated with heptane and allowed to stand for about five days. Theresultant solid was collected by filtration and dried, yielding 144.4grams of crude product. The crude product was combined with materialprepared by a similar route, yielding a total of 157.8 grams ofmaterial. The combined product was subjected to column chromatography onsilica gel, yielding 83.2 grams of an orange solid. The solid wasslurried with warm ethyl acetate, and the insoluble product wascollected by filtration. The product was washed with ethyl acetate, andthe wash and filtrate from above were combined. The process ofconcentrating the filtrate, and slurrying the solid residue was repeatedtwice more, yielding a total of 51.9 grams of title compound. The NMRspectrum was consistent with the proposed structure.

An alternate method for preparing3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneis the following:

A solution of 19.2 grams (0.050 mole) of3-(6-amino-4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione,3.0 grams (0.056 mole) of ammonium chloride, and 50 mL of water in 100mL of ethanol was stirred, and 11.2 grams (0.201 mole) of iron powder(325 mesh) was added in one portion. Upon completion of addition, thereaction mixture was heated at reflux for one hour. The reaction mixturewas allowed to cool to ambient temperature, then it was filtered throughdiatomaceous earth to remove the iron powder. The filter cake was washedwith 200 mL of acetone, and the wash was combined with the filtrate. Thecombination was stirred with decolorizing carbon and filtered. Thefiltrate was concentrated under reduced pressure, yielding a dark brownoil. The oil was then taken up in 200 mL of methylene chloride andwashed with three 100 mL portions of an aqueous saturated sodiumbicarbonate solution. The organic layer was dried with magnesiumsulfate, filtered, and concentrated under reduced pressure, yielding12.8 grams of title compound. The NMR spectrum was consistent with theproposed structure.

Step E Compound 367

A stirred solution of 1.0 grams (0.0028 mole) of3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneand 0.28 mL (0.0035 mole) of pyridine in 10 mL chloroform was cooled to5° C. and 0.27 mL (0.0031 mole) of propionyl chloride was addeddropwise. Upon completion of addition, the mixture was allowed to warmto ambient temperature were it stirred for about 18 hours. The mixturewas cooled to 5° C. and 5.0 mL (0.054 mole) of phosphorous oxychloridewas added in one portion. Upon completion of addition, the reactionmixture was allowed to warm to ambient temperature where it stirred forabout 18 hours. At the conclusion of this period, the reaction mixturewas poured into 200 mL of cold water, the resulting mixture was stirredfor one hour, then it was extracted with three 50 mL portions ofchloroform. The combined extracts were dried with magnesium sulfate andfiltered. The filtrate was concentrated under reduced pressure, yielding0.15 gram of an orange residue. The aqueous layer was made basic with anaqueous saturated sodium bicarbonate solution to a pH of 3-4. Theresulting mixture was extracted with three 50 mL portions of methylenechloride. The extracts were combined, dried with magnesium sulfate, andfiltered. The filtrate was concentrated under reduced pressure, yielding0.70 gram of a yellow residue. The yellow residue was triturated withhot heptane. The resulting solid was collected by filtration and washedwith heptane, yielding 0.67 gram of Compound 367, m.p. 150-155° C. TheNMR spectrum was consistent with the proposed structure.

EXAMPLE 7 Synthesis of3-(2-t-Butyl-4-Chloro-6-Fluorobenzimidazol-7-yl)-1-Methyl-6-Trifluoromethyl-2,4(1H,3H)-Pyrimidinedione

(Compound 369)

To a stirred solution of 1.0 grams (0.0028 mole) of3-(5,6-diamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione,15.0 mL of ethanol, and 4 mL of 5 M hydrochloric acid was added 1.2 mL(0.0057 mole) of 2,2,6,6-tetramethyl-3,5-heptanedione. Upon completionof addition, the reaction mixture was heated to reflux where it stirredfor ten minutes. At the conclusion of this period, the reaction mixturewas analyzed by TLC, which indicated that the reaction was not complete.The reaction mixture was stirred at reflux for an additional two hours.After this time, the reaction mixture was again analyzed by TLC, whichagain indicated that the reaction was still not complete. As a result,an additional 1.0 mL (0.0048 mole) of2,2,6,6-tetramethyl-3,5-heptanedione was added. Upon completion ofaddition, the reaction mixture was stirred at reflux for three days. Atthe conclusion of this period, more ethanol was added to replace thatwhich evaporated, and the reaction mixture was analyzed by TLC for athird time. The reaction mixture was allowed to cool to ambienttemperature, poured into 100 mL of an aqueous saturated sodiumbicarbonate solution, and 100 mL of chloroform was added. The aqueouslayer was separated and washed with two 100 mL portions of chloroform.The chloroform layer and washes were combined, dried with magnesiumsulfate, and filtered. The filtrate was treated with decolorizing carbonand stirred. The mixture was filtered and concentrated under reducedpressure to yield a red oil. The oil was taken up in heptane. Theresulting solid was collected by filtration and washed with heptane toyield a tan solid. The solid was purified by column chromatography onsilica gel, yielding 0.36 gram of Compound 369, m.p. 125-130° C. The NMRspectrum was consistent with the proposed structure.

EXAMPLE 8 Synthesis of3-(7-Chloro-Fluoro-2-Trifluoromethylindol-4-yl)-1-Methyl-6-Trifluoromethyl-2,4(1H,3H)-Pyrimidinedione

(Compound 500)

Step A3-[5-(1-trifluoromethylethylidenehydrazino)-4-chloro-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A solution of 3.37 grams (0.010 mole) of3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionein 80 mL of concentrated hydrochloric acid was stirred at 25° C. for 20minutes. After this time, the solution was cooled to 10° C. and asolution of 0.69 gram (0.010 mole) of sodium nitrite in 10 mL of waterwas slowly added. Upon completion of addition, the mixture was stirredfor one hour at 10° C. and then a solution of 5.64 grams (0.025 mole) oftin (II) chloride dihydrate in 40 mL of concentrated hydrochloric acidwas slowly added. Upon completion of addition, the reaction mixture waswarmed to 25° C. where it stirred for one hour. At the conclusion ofthis period, 1.12 grams (0.010 mole) of trifluoroacetone was added andthe resulting solid was collected by filtration, yielding 3.13 grams oftitle compound, m.p. 213-214° C. The NMR spectrum was consistent withthe proposed structure.

Step B Compound 500

A stirred solution of 2.0 grams (0.0044 mole) of3-[5-(1-trifluoromethylethylidenehydrazino)-4-chloro-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedionein 80 mL of polyphosphoric acid was heated at 80° C. for 20 minutes.After this time, the reaction mixture was allowed to cool to 25° C.where it was diluted with water. The resulting solid was collected byfiltration, yielding 0.73 gram of Compound 500, m.p. 208-210° C. The NMRspectrum was consistent with the proposed structure.

EXAMPLE 9 Synthesis of347-Chloro-2-Ethoxycarbonylindol4-yl)-4,5,6,7-Tetrahydro-1H-Isoindole-1,3(2H)-Dione

(Compound 595)

Step A 3-(1-ethoxycarbonylethylidenehydrazino)-4-chloronitrobenzene

This compound was prepared in the manner of Step A, Example 1, using,17.25 grams (0.10 mole) of 2-chloro-5-nitroaniline, 6.9 grams (0.10mole) of sodium nitrite, 56.4 grams (0.25 mole) of tin (II) chloridedihydrate, 11.61 grams (0.10 mole) of ethyl pyruvate, 30 mL of water,and 100 mL of concentrated hydrochloric acid. This preparation differsin that ethyl pyruvate was used rather than trifluoroacetone. The yieldof title compound was 19.4 grams. The NMR spectrum was consistent withthe proposed structure.

Step B 7-chloro-2-ethoxycarbonyl-4-nitroindole

This compound was prepared in the manner of Step B, Example 8, using14.0 grams (0.050 mole) of3-(1-ethoxycarbonylethylidenehydrazino)-4-chloronitrobenzene in 100 mLof polyphosphoric acid. The yield of title compound was 0.4 gram. TheNMR spectrum was consistent with the proposed structure.

Step C 7-amino-4-chloro-2-ethoxycarbonylindole

A stirred solution of 2.68 grams (0.01 mole) of4-chloro-2-ethoxycarbonyl-7-nitroindole, 80 mL of acetic acid, and 15 mLof water was heated to 65° C., and 18.3 grams (0.048 mole) of ironpowder was slowly added during a 20 minute period. Upon completion ofaddition, the reaction mixture was allowed to cool to 25° C. where itstirred for one hour. After this time, the reaction mixture was pouredinto water, and the resulting mixture was filtered through diatomaceousearth. The filter cake was washed thoroughly with ethyl acetate. Theorganic layer was dried with magnesium sulfate and filtered. Thefiltrate was concentrated under reduced pressure a residue. The residuewas purified by column chromatography, yielding 0.4 gram of titlecompound. The NMR spectrum was consistent with the proposed structure.

Step D Compound 595

A stirred solution of 0.4 gram (0.0016 mole) of7-amino-4-chloro-2-ethoxycarbonylindole and 0.26 gram (0.0016 mole) of3,4,5,6-tetrahydrophhalic anhydride in 80 mL of acetic acid was heatedat reflux for about 18 hours. After this time, the reaction mixture wasextracted with several portions of diethyl ether. The organic extractswere combined, dried with magnesium sulfate, and filtered. The filtratewas concentrated under reduced pressure to a residue. The residue waspurified by column chromatography on silica gel, yielding 0.47 gram ofCompound 595. The NMR spectrum was consistent with the proposedstructure.

                  TABLE 1                                                         ______________________________________                                        Benzoxazoles                                                                   ##STR15##                                                                    where A is nitrogen double bonded to position 2 and B is O; J is               ##STR16##                                                                    Compound No. X        R         R3                                            ______________________________________                                        1            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.3                                      2            4-Cl, 6-F                                                                              CH.sub.3  C.sub.2 H.sub.5                               3            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.2 CN                                   4            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.2 CH═CH.sub.2                      5            4-Cl, 6-F                                                                              CH.sub.3  NH.sub.2                                      6            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.2 C.tbd.CH                             7            4-Cl, 6-F                                                                              CH.sub.3  C.sub.3 H.sub.7                               8            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.2 OCH.sub.3                            9            4-Cl, 6-F                                                                              CH.sub.3  CH.sub.2 CO.sub.2 C.sub.2 H.sub.5             ______________________________________                                    

                                      TABLE 2                                     __________________________________________________________________________     ##STR17##                                                                     ##STR18##                                                                     ##STR19##                                                                     ##STR20##                                                                     ##STR21##                                                                                        Double                                                                        Bond                                                      No.                                                                              A        B       Posit'n                                                                           X     R            J                                  __________________________________________________________________________     10                                                                              N        O       1-2 4-Cl  CH.sub.3     J1                                  11                                                                              N        O       1-2 4-Cl  C.sub.2 H.sub.5                                                                            J1                                  12                                                                              N        O       1-2 4-Cl  CH(CH.sub.3).sub.2                                                                         J1                                  13                                                                              N        O       1-2 4,6-Cl.sub.2                                                                        CH.sub.3     J1                                  14                                                                              N        O       1-2 4,6-Cl.sub.2                                                                        C.sub.2 H.sub.5                                                                            J1                                  15                                                                              N        O       1-2 4,6-Cl.sub.2                                                                        C.sub.2 H.sub.5                                                                            J1                                  16                                                                              N        O       1-2 4-Br, 6-F                                                                           CH.sub.3     J1                                  17                                                                              N        O       1-2 4-CF.sub.3, 6-F                                                                     CH.sub.3     J1                                  18                                                                              N        O       1-2 4,6-F.sub.2                                                                         CH.sub.3     J1                                  19                                                                              N        O       1-2 4-CN, 6-F                                                                           CH.sub.3     J1                                  20                                                                              N        O       1-2 4-OCF.sub.3, 6-F                                                                    CH.sub.3     J1                                  21                                                                              N        O       1-2 4-Br, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                  22                                                                              N        O       1-2 4-CN, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                  23                                                                              N        O       1-2 4-CN, 6-F                                                                           CH(CH.sub.3).sub.2                                                                         J1                                  24                                                                              N        O       1-2 4-CH.sub.3, 6-F                                                                     CH.sub.3     J1                                  25                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                  26                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.3 H.sub.7                                                                            J1                                  27                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.4 H.sub.9                                                                            J1                                  28                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH(CH.sub.3).sub.2                                                                         J1                                  29                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH(CH.sub.3).sub.2                                                                J1                                  30                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.3                                                                          J1                                  31                                                                              N        O       1-2 4-Cl, 6-F                                                                           phenyl       J1                                  32                                                                              N        O       1-2 4-Cl, 6-F                                                                           phenylmethyl J1                                  33                                                                              N        O       1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                  34                                                                              N        O       1-2 4-Cl, 6-F                                                                           CCl.sub.2    J1                                  35                                                                              N        O       1-2 4-Cl, 6-F                                                                           Cl           J1                                  36                                                                              N        O       1-2 4-Cl, 6-F                                                                           OH           J1                                  37                                                                              N        O       1-2 4-Cl, 6-F                                                                           Br           J1                                  38                                                                              N        O       1-2 4-Cl, 6-F                                                                           NH.sub.2     J1                                  39                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHCH.sub.3   J1                                  40                                                                              N        O       1-2 4-Cl, 6-F                                                                           N(CH.sub.3).sub.2                                                                          J1                                  41                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHCH.sub.2 CO.sub.2 CH.sub.3                                                               J1                                  42                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHSO.sub.2 CH.sub.3                                                                        J1                                  43                                                                              N        O       1-2 4-Br, 6-F                                                                           NHCOCH.sub.3 J1                                  44                                                                              N        O       1-2 4-Cl, 6-F                                                                           morpholino   J1                                  45                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHSO.sub.2 C.sub.6 H.sub.5                                                                 J1                                  46                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHSO.sub.2 CH.sub.2 C.sub.6 H.sub.5                                                        J1                                  47                                                                              N        O       1-2 4-Cl, 6-F                                                                           N(CH.sub.3)SO.sub.2 CH.sub.3                                                               J1                                  48                                                                              N        O       1-2 4-Cl, 6-F                                                                           NHPO(OCH.sub.3).sub.2                                                                      J1                                  49                                                                              N        O       1-2 4-Br, 6-F                                                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                 J1                                  50                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 CO.sub.2 CH.sub.3                                                          J1                                  51                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH═CHCO.sub.2 CH.sub.3                                                                 J1                                  52                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH═C(Cl)CO.sub.2 CH.sub.3                                                              J1                                  53                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH(Cl)CO.sub.2 CH.sub.3                                                           J1                                  54                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.3    J1                                  55                                                                              N        O       1-2 4-Cl, 6-F                                                                           OC.sub.2 H.sub.5                                                                           J1                                  56                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3).sub.2                                                                        J1                                  57                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CH═CH.sub.2                                                                  J1                                  58                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 C(CH.sub.3)═CH.sub.2                                                         J1                                  59                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CCH                                                                              J1                                  60                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                         J1                                  61                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CO.sub.2 CH.sub.3                                                             J1                                  62                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CN J1                                  63                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CONH.sub.2                                                                       J1                                  64                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CONHCH.sub.3                                                                     J1                                  65                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CONH.sub.2                                                                    J1                                  66                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CONHCH.sub.3                                                                  J1                                  67                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CO.sub.2 H                                                                       J1                                  68                                                                              N        O       1-2 4-Cl, 6-F                                                                           phenoxy      J1                                  69                                                                              N        O       1-2 4-Cl, 6-F                                                                           p-OC.sub.6 H.sub.4 OCH(CH.sub.3)CO.sub.2                                      CH.sub.3     J1                                  70                                                                              N        O       1-2 4-Cl, 6-F                                                                           4-chlorophenoxy                                                                            J1                                  71                                                                              N        O       1-2 4-Cl, 6-F                                                                           phenylmethoxy                                                                              J1                                  72                                                                              N        O       1-2 4-Cl, 6-F                                                                           CN           J1                                  73                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                  74                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 H   J1                                  75                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 Na  J1                                  76                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONH.sub.2   J1                                  77                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J1                                  78                                                                              N        O       1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J1                                  79                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J1                                  80                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 NHOCH.sub.3                                                                       J1                                  81                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.3    J1                                  82                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.2 CO.sub.2 CH.sub.3                                                                J1                                  83                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.2 CONH.sub.2                                                                       J1                                  84                                                                              N        O       1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J1                                  85                                                                              N        O       1-2 4-Cl, 6-F                                                                           SH           J1                                  86                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OH  J1                                  87                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J1                                  88                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                  89                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 OH                                                                         J1                                  90                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH(CH.sub.3)OH                                                                    J1                                  91                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 C(CH.sub.3).sub.2 OH                                                              J1                                  92                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                  93                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH(CH.sub.3).sub.2 OCOCH.sub.3                                                             J1                                  94                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH.sub.3                                                                    J1                                  95                                                                              N        O       1-2 4-Cl, 6-F                                                                           CHBr.sub.2   J1                                  96                                                                              N        O       1-2 4-Br, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J1                                  97                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.2 CCH                                                                     J1                                  98                                                                              N        O       1-2 4-Br, 6-F                                                                           NH.sub.2     J1                                  99                                                                              N        O       1-2 4-Br, 6-F                                                                           phenoxymethyl                                                                              J1                                 100                                                                              N        O       1-2 4-Br, 6-F                                                                           N(COCH.sub.3).sub.2                                                                        J1                                 101                                                                              N        O       1-2 4-Br, 6-F                                                                           CH.sub.2 OCOCH.sub.3                                                                       J1                                 102                                                                              N        O       1-2 4-Br, 6-F                                                                           4-chlorophenoxymethyl                                                                      J1                                 103                                                                              N        O       1-2 4-Br, 6-F                                                                           CH(Ph)OCOCH.sub.3                                                                          J1                                 104                                                                              N        O       1-2 4-Br, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                 105                                                                              N        O       1-2 4-Br, 6-F                                                                           CO.sub.2 H   J1                                 106                                                                              N        O       1-2 4-Br, 6-F                                                                           OCH.sub.2 CCH                                                                              J1                                 107                                                                              N        O       1-2 4-Br, 6-F                                                                           OCH(CH.sub.3).sub.2                                                                        J1                                 108                                                                              N        O       1-2 4-Br, 6-F                                                                           NHSO.sub.2 CH.sub.3                                                                        J1                                 109                                                                              N        O       1-2 4-Br, 6-F                                                                           OCH.sub.3    J1                                 110                                                                              N        O       1-2 4-Br, 6-F                                                                           OCH.sub.2 CH═CH.sub.2                                                                  J1                                 111                                                                              N        O       1-2 4-Cl, 6-F                                                                           (CH.sub.3)(CN)OH                                                                           J1                                 112                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.3     J2                                 113                                                                              N        O       1-2 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J2                                 114                                                                              N        O       1-2 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J2                                 115                                                                              N        O       1-2 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J2                                 116                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J2                                 117                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CO.sub.2 CH.sub.3                                                                 J2                                 118                                                                              N        O       1-2 4-Cl, 6-F                                                                           phenoxymethyl                                                                              J2                                 119                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J2                                 120                                                                              N        O       1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J2                                 121                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J2                                 122                                                                              N        O       1-2 4-Cl, 6-F                                                                           Phenyl       J2                                 123                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.3    J2                                 124                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J2                                 125                                                                              N        O       1-2 4-Cl, 6-F                                                                           Benzyl       J2                                 126                                                                              N        O       1-2 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J2                                 127                                                                              N        O       1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J2                                 128                                                                              N        O       1-2 4-Cl, 6-F                                                                           CF.sub.3     J2                                 129                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                                       J2                                 130                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J2                                 131                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.3     J3                                 132                                                                              N        O       1-2 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J3                                 133                                                                              N        O       1-2 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J3                                 134                                                                              N        O       1-2 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J3                                 135                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OH  J3                                 136                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J3                                 137                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J3                                 138                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J3                                 139                                                                              N        O       1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J3                                 140                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J3                                 141                                                                              N        O       1-2 4-Cl, 6-F                                                                           Phenyl       J3                                 142                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.3    J3                                 143                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J3                                 144                                                                              N        O       1-2 4-Cl, 6-F                                                                           Benzyl       J3                                 145                                                                              N        O       1-2 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J3                                 146                                                                              N        O       1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J3                                 147                                                                              N        O       1-2 4-Cl, 6-F                                                                           CF.sub.3     J3                                 148                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                                       J3                                 149                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J3                                 150                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                                       J3                                 151                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 152                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 Na  J3                                 153                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J3                                 154                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CO.sub.2 CH.sub.3                                                                J3                                 155                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CO.sub.2 CH.sub.3                                                             J3                                 156                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CH═CH.sub.2                                                                  J3                                 157                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CCH                                                                              J3                                 158                                                                              N        O       1-2 4-Cl, 6-F                                                                           OH           J3                                 159                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.3    J3                                 160                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3).sub.2                                                                        J3                                 161                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.3     J4                                 162                                                                              N        O       1-2 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J4                                 163                                                                              N        O       1-2 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J4                                 164                                                                              N        O       1-2 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J4                                 165                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OH  J4                                 166                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J4                                 167                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J4                                 168                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J4                                 169                                                                              N        O       1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J4                                 170                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J4                                 171                                                                              N        O       1-2 4-Cl, 6-F                                                                           Phenyl       J4                                 172                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.3    J4                                 173                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J4                                 174                                                                              N        O       1-2 4-Cl, 6-F                                                                           Benzyl       J4                                 175                                                                              N        O       1-2 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J4                                 176                                                                              N        O       1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J4                                 177                                                                              N        O       1-2 4-Cl, 6-F                                                                           CF.sub.3     J4                                 178                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                                       J4                                 179                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J4                                 180                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                                       J4                                 181                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 182                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 Na  J4                                 183                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J4                                 184                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CO.sub.2 CH.sub.3                                                                J4                                 185                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CO.sub.2 CH.sub.3                                                             J4                                 186                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CH═CH.sub.2                                                                  J4                                 187                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 C.tbd.CH                                                                         J4                                 188                                                                              N        O       1-2 4-Cl, 6-F                                                                           OH           J4                                 189                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.3    J4                                 190                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3).sub.2                                                                        J4                                 191                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.3     J5                                 192                                                                              N        O       1-2 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J5                                 193                                                                              N        O       1-2 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J5                                 194                                                                              N        O       1-2 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J5                                 195                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OH  J5                                 196                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J5                                 197                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J5                                 198                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J5                                 199                                                                              N        O       1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J5                                 200                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J5                                 201                                                                              N        O       1-2 4-Cl, 6-F                                                                           Phenyl       J5                                 202                                                                              N        O       1-2 4-Cl, 6-F                                                                           SCH.sub.3    J5                                 203                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J5                                 204                                                                              N        O       1-2 4-Cl, 6-F                                                                           Benzyl       J5                                 205                                                                              N        O       1-2 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J5                                 206                                                                              N        O       1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J5                                 207                                                                              N        O       1-2 4-Cl, 6-F                                                                           CF.sub.3     J5                                 208                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCO.sub.2 CH.sub.3                                                       J5                                 209                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J5                                 210                                                                              N        O       1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                                       J5                                 211                                                                              N        O       1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 212                                                                              N        O       1-2 4-Cl, 6-F                                                                           CO.sub.2 Na  J5                                 213                                                                              N        O       1-2 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J5                                 214                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CO.sub.2 CH.sub.3                                                                J5                                 215                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3)CO.sub.2 CH.sub.3                                                             J5                                 216                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CH═CH.sub.2                                                                  J5                                 217                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.2 CCH                                                                              J5                                 218                                                                              N        O       1-2 4-Cl, 6-F                                                                           OH           J5                                 219                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH.sub.3    J5                                 220                                                                              N        O       1-2 4-Cl, 6-F                                                                           OCH(CH.sub.3).sub.2                                                                        J5                                 221                                                                              O        CH      2-3 4-Cl  CH.sub.3     J1                                 222                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 223                                                                              O        CH      2-3 4-Cl, 6-F                                                                           n-propyl     J1                                 224                                                                              O        CH      2-3 4-Cl, 6-F                                                                           isopropyl    J1                                 225                                                                              O        CH      2-3 4-Cl  n-butyl      J1                                 226                                                                              O        CH      2-3 4-Cl  t-butyl      J1                                 227                                                                              O        CH      2-3 4-Cl, 6-F                                                                           t-butyl      J1                                 228                                                                              O        CH      2-3 4,6-F.sub.2                                                                         t-butyl      J1                                 229                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)C.sub.3 H.sub.7                                                                J1                                 230                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH═CH.sub.2                                                                            J1                                 231                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3)═CH.sub.2                                                                   J1                                 232                                                                              O        CH      2-3 4-Cl  CH.sub.2 Br  J1                                 233                                                                              O        CH      2-3 4-Cl  CHBr.sub.2   J1                                 234                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(Cl)CH.sub.3                                                                             J1                                 235                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(F)CH.sub.3                                                                              J1                                 236                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 Cl                                                                       J1                                 237                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 F                                                                        J1                                 238                                                                              O        CH      2-3 4-Cl  CH.sub.2 OH  J1                                 239                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J1                                 240                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J1                                 241                                                                              O        CH      2-3 4-Cl  C(CH.sub.3).sub.2 OH                                                                       J1                                 242                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                 243                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH(CH.sub.3)OH                                                                    J1                                 244                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OC(CH.sub.3).sub.3                                                             J1                                 245                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(OC.sub.2 H.sub.5).sub.2                                                                 J1                                 246                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH.sub.3                                                                    J1                                 247                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH(CH.sub.3).sub.2                                                          J1                                 248                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOPh                                                                          J1                                 249                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCONHCH.sub.3                                                                  J1                                 250                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCONHCH.sub.2 Ph                                                               J1                                 251                                                                              O        CH      2-3 4-Cl  C(CH.sub.3).sub.2 OCH.sub.3                                                                J1                                 252                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                                      J1                                 253                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                 254                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NH.sub.2                                                                 J1                                 255                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J1                                 256                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CH.sub.2 CN                                                              J1                                 257                                                                              O        CH      2-3 4-Cl  CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                                          J1                                 258                                                                              O        CH      2-3 4-Cl  CH═NOH   J1                                 259                                                                              O        CH      2-3 4-Cl  CH═NOCH.sub.3                                                                          J1                                 260                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              J1                                 261                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                            J1                                 262                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 H                                                               J1                                 263                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                                        J1                                 264                                                                              O        CH      2-3 4-Cl  Phenyl       J1                                 265                                                                              O        CH      2-3 4-Cl  CHO          J1                                 266                                                                              O        CH      2-3 4-Cl  CO.sub.2 H   J1                                 267                                                                              O        CH      2-3 H     CO.sub.2 C.sub.2 H.sub.5                                                                   J1                                 268                                                                              O        CH      2-3 4-Cl  CO.sub.2 C.sub.2 H.sub.5                                                                   J1                                 269                                                                              O        CH      2-3 4-Cl  CONH.sub.2   J1                                 270                                                                              O        CH      2-3 4-Cl  CONHCH.sub.3 J1                                 271                                                                              O        CH      2-3 4-Cl  CON(CH.sub.3).sub.2                                                                        J1                                 272                                                                              O        CH      2-3 4-Cl  NHCO.sub.2 C(CH.sub.3).sub.3                                                               J1                                 273                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CONH.sub.2   J1                                 274                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CONH(CH.sub.3)                                                                             J1                                 275                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J1                                 276                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 H   J1                                 277                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 278                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 OH  J1                                 279                                                                              O        CH      2-3 4-Cl, 6-F                                                                           3,4-dimethoxyphenyl                                                                        J1                                 280                                                                              O        CH      2-3 4-Cl, 6-F                                                                           Phenyl       J1                                 281                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J2                                 282                                                                              O        CH      2-3 4-Cl, 6-F                                                                           n-propyl     J2                                 283                                                                              O        CH      2-3 4-Cl, 6-F                                                                           isopropyl    J2                                 284                                                                              O        CH      2-3 4-Cl, 6-F                                                                           t-butyl      J2                                 285                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)C.sub.3 H.sub.7                                                                J2                                 286                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH═CH.sub.2                                                                            J2                                 287                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3)═CH.sub.2                                                                   J2                                 288                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(Cl)CH.sub.3                                                                             J2                                 289                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(F)CH.sub.3                                                                              J2                                 290                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 Cl                                                                       J2                                 291                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 F                                                                        J2                                 292                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J2                                 293                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J2                                 294                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J2                                 295                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH(CH.sub.3)OH                                                                    J2                                 296                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OC(CH.sub.3).sub.3                                                             J2                                 297                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(OC.sub.2 H.sub.5).sub.2                                                                 J2                                 298                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH.sub.3                                                                    J2                                 299                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH(CH.sub.3).sub.2                                                          J2                                 300                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOPh                                                                          J2                                 301                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCONHCH.sub.3                                                                  J2                                 302                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCONHCH.sub.2 Ph                                                               J2                                 303                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                                      J2                                 304                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J2                                 305                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NH.sub.2                                                                 J2                                 306                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J2                                 307                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CH.sub.2 CN                                                              J2                                 308                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OCOCH.sub.3                                                              J2                                 309                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OCONHCH.sub.3                                                            J2                                 310                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 H                                                               J2                                 311                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                                        J2                                 312                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CONH.sub.2   J2                                 313                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CONH(CH.sub.3)                                                                             J2                                 314                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J2                                 315                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 H   J2                                 316                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J2                                 317                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 OH  J2                                 318                                                                              O        CH      2-3 4-Cl, 6-F                                                                           3,4-dimethoxyphenyl                                                                        J2                                 319                                                                              O        CH      2-3 4-Cl, 6-F                                                                           Phenyl       J2                                 320                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J3                                 321                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 322                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(Cl)CH.sub.3                                                                             J3                                 323                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(F)CH.sub.3                                                                              J3                                 324                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 Cl                                                                       J3                                 325                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 F                                                                        J3                                 326                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J3                                 327                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J3                                 328                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J3                                 329                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                                      J3                                 330                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J3                                 331                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CH.sub.2 CN                                                              J3                                 332                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                                        J3                                 333                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J3                                 334                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J4                                 335                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 336                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(Cl)CH.sub.3                                                                             J4                                 337                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(F)CH.sub.3                                                                              J4                                 338                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 Cl                                                                       J4                                 339                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 F                                                                        J4                                 340                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J4                                 341                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J4                                 342                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J4                                 343                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                                      J4                                 344                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J4                                 345                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CH.sub.2 CN                                                              J4                                 346                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                                        J4                                 347                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J4                                 348                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J5                                 349                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 350                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(Cl)CH.sub.3                                                                             J5                                 351                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(F)CH.sub.3                                                                              J5                                 352                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 Cl                                                                       J5                                 353                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 F                                                                        J5                                 354                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J5                                 355                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OH                                                                             J5                                 356                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J5                                 357                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCH.sub.2 OCH.sub.3                                                      J5                                 358                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J5                                 359                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CH.sub.2 CN                                                              J5                                 360                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                                                        J5                                 361                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J5                                 362                                                                              NH       N       2-3 4-Cl, 6-F                                                                           H            J1                                 363                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 364                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CHF.sub.2    J1                                 365                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 366                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CClF.sub.2   J1                                 367                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 368                                                                              NH       N       2-3 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J1                                 369                                                                              NH       N       2-3 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J1                                 370                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J1                                 371                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OC(O)CH.sub.3                                                            J1                                 372                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 CO.sub.2 C.sub.2 H.sub.5                                                   J1                                 373                                                                              NH       N       2-3 4-Cl, 6-F                                                                           Cyclohexyl   J1                                 374                                                                              NH       N       2-3 4-Cl, 6-F                                                                           Adamantyl    J1                                 375                                                                              NH       N       2-3 4-Cl, 6-F                                                                           Phenyl       J1                                 376                                                                              NH       N       2-3 4-Cl, 6-F                                                                           Benzyl       J1                                 377                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)C.sub.6 H.sub.5                                                                J1                                 378                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 OC.sub.6 H.sub.5                                                                  J1                                 379                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 C.sub.8 H.sub.5                                                            J1                                 380                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.3 H.sub.6 C.sub.6 H.sub.5                                                            J1                                 381                                                                              NH       N       2-3 4-Cl, 6-F                                                                           2-chlorophenylmethyl                                                                       J1                                 382                                                                              NH       N       2-3 4-Cl, 6-F                                                                           3-chlorophenylmethyl                                                                       J1                                 383                                                                              NH       N       2-3 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J1                                 384                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 385                                                                              NH       N       2-3 4-Cl, 6-F                                                                           Furan-2-yl   J1                                 386                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 Cl  J1                                 387                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 Cl                                                              J1                                 388                                                                              NH       N       2-3 4-Cl, 6-F                                                                           OC.sub.2 H.sub.5                                                                           J1                                 389                                                                              N        NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 390                                                                              N        NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 391                                                                              N        NH      1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 392                                                                              N        NH      1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 393                                                                              N        NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 394                                                                              N        NH      1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 395                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 396                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 397                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 398                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 399                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 400                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 401                                                                              N        NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.2 CH.sub.3                                                                 J1                                 402                                                                              N        NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 403                                                                              N        NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 404                                                                              NH       NH      --  4-NO.sub.2, 6-F                                                                     CF.sub.3     J1                                 405                                                                              N.sup.- H.sub.3 N.sup.+ CH(CH.sub.3).sub.2                                             N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 406                                                                              NCH.sub.3                                                                              N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 407                                                                              NCH.sub.3                                                                              NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 408                                                                              N        NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 409                                                                              N        NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 410                                                                              N        NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 411                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 412                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 413                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 414                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 415                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 416                                                                              N        NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 417                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 418                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 419                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 420                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 421                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 422                                                                              N        NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 423                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 424                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 425                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 426                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 427                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 428                                                                              N        NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 429                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 430                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 431                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 432                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 433                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 434                                                                              N        NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 435                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 436                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 437                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 438                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 439                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 440                                                                              N        NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 441                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 442                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 443                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 444                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 445                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 446                                                                              N        NCH.sub.2 CCH                                                                         1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 447                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 448                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 449                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 450                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 451                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 452                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 453                                                                              N        NCF.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 454                                                                              N        NCF.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 455                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 456                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 457                                                                              N        NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 458                                                                              N        NCF.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 459                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J2                                 460                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J2                                 461                                                                              NH       N       2-3 4-Cl, 6-F                                                                           isopropyl    J2                                 462                                                                              NH       N       2-3 4-Cl, 6-F                                                                           t-butyl      J2                                 463                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J2                                 464                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J2                                 465                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J3                                 466                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 467                                                                              NH       N       2-3 4-Cl, 6-F                                                                           isopropyl    J3                                 468                                                                              NH       N       2-3 4-Cl, 6-F                                                                           t-butyl      J3                                 469                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J3                                 470                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J3                                 471                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J4                                 472                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 473                                                                              NH       N       2-3 4-Cl, 6-F                                                                           isopropyl    J4                                 474                                                                              NH       N       2-3 4-Cl, 6-F                                                                           t-butyl      J4                                 475                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J4                                 476                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J4                                 477                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.3     J5                                 478                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 479                                                                              NH       N       2-3 4-Cl, 6-F                                                                           isopropyl    J5                                 480                                                                              NH       N       2-3 4-Cl, 6-F                                                                           t-butyl      J5                                 481                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J5                                 482                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J5                                 483                                                                              NH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 484                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J1                                 485                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J1                                 486                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J1                                 487                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.2 OH  J1                                 488                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J1                                 489                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                 490                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CONHCH.sub.3 J1                                 491                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J1                                 492                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 493                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.2 CH.sub.3                                                                 J1                                 494                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           Phenyl       J1                                 495                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 496                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J1                                 497                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           Benzyl       J1                                 498                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J1                                 499                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J1                                 500                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 501                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                 502                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J1                                 503                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                                       J1                                 504                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 505                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 Na  J1                                 506                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J1                                 507                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CHFCH.sub.3  J1                                 508                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                        J1                                 509                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 510                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 511                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 512                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 513                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 514                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 515                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CHFCH.sub.3  J1                                 516                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J1                                 517                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                          J1                                 518                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 CN                                                                       J1                                 519                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                 520                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                 521                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 NHSO.sub.2 CH.sub.3                                                      J1                                 522                                                                              CH       NCH.sub.3                                                                             1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.2 CH.sub.3                                                                 J1                                 523                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 524                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 525                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 526                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 527                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 528                                                                              CH       NC.sub.2 H.sub.5                                                                      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 529                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 530                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 531                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 532                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 533                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 534                                                                              CH       NC.sub.4 H.sub.9                                                                      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 535                                                                              CH       NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 536                                                                              CH       NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 537                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 538                                                                              CH       NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 539                                                                              CH       NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 540                                                                              CH       NCH.sub.2 OCH.sub.3                                                                   1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 541                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 542                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 543                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J 1                                544                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 545                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 546                                                                              CH       NCO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 547                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 548                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 549                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 550                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 551                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 552                                                                              CH       NSO.sub.2 CH.sub.3                                                                    1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 553                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 554                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 555                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 556                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 557                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 558                                                                              CH       NCH.sub.2 CHCH.sub.2                                                                  1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 559                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 560                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 561                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 562                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 563                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 564                                                                              CH       NCH.sub.2 C.tbd.CH                                                                    1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 565                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 566                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 567                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 568                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 569                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 570                                                                              CH       NCH.sub.2 CO.sub.2 Me                                                                 1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 571                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           CH.sub.3     J1                                 572                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 573                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           isopropyl    J1                                 574                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           t-butyl      J1                                 575                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 576                                                                              CH       NCH.sub.2 CHF.sub.2                                                                   1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 577                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J2                                 578                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J2                                 579                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           isopropyl    J2                                 580                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           t-butyl      J2                                 581                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J2                                 582                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J2                                 583                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J3                                 584                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 585                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           isopropyl    J3                                 586                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           t-butyl      J3                                 587                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J3                                 588                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J3                                 589                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J4                                 590                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 591                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           isopropyl    J4                                 592                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           t-butyl      J4                                 593                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J4                                 594                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J4                                 595                                                                              CH       NH      1-2 4-Cl  CO.sub.2 CH.sub.2 CH.sub.3                                                                 J5                                 596                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CH.sub.3     J5                                 597                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           C.sub.2 H.sub.3                                                                            J5                                 598                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           isopropyl    J5                                 599                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           t-butyl      J5                                 600                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J5                                 601                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J5                                 602                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J7                                 603                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           n-C.sub.3 H.sub.7                                                                          J1                                 604                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           i-C.sub.3 H.sub.7                                                                          J1                                 605                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-C.sub.4 H.sub.9                                                                          J1                                 606                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 OH  J1                                 607                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CH.sub.2 OH                                                                       J1                                 608                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                 609                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CONHCH.sub.3 J1                                 610                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CON(CH.sub.3).sub.2                                                                        J1                                 611                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 612                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           Phenyl       J1                                 613                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.2 CF.sub.3                                                                          J1                                 614                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 OCH.sub.3                                                                         J1                                 615                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           Benzyl       J1                                 616                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           4-chlorophenylmethyl                                                                       J1                                 617                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J1                                 618                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 619                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OCOCH.sub.3                                                              J1                                 620                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OH                                                              J1                                 621                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3                                                       J1                                 622                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 623                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 Na  J1                                 624                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CONHSO.sub.2 CH.sub.3                                                                      J1                                 625                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CHFCH.sub.3  J1                                 626                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                        J1                                 627                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J2                                 628                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J2                                 629                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J2                                 630                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J2                                 631                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J2                                 632                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J2                                 633                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J3                                 634                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 635                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J3                                 636                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J3                                 637                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J3                                 638                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J3                                 639                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J4                                 640                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 641                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J4                                 642                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J4                                 643                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J4                                 644                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J4                                 645                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J5                                 646                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 647                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J5                                 648                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J5                                 649                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J5                                 650                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J5                                 651                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 652                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 653                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           isopropyl    J1                                 654                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           t-butyl      J1                                 655                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 656                                                                              NH       CCH.sub.3                                                                             2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 657                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 658                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 659                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           isopropyl    J1                                 660                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           t-butyl      J1                                 661                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 662                                                                              NH       CCH.sub.2 CH.sub.3                                                                    2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 663                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           CH.sub.3     J1                                 664                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 665                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           isopropyl    J1                                 666                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           t-butyl      J1                                 667                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 668                                                                              NH       CCH.sub.2 CHF.sub.2                                                                   2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J1                                 669                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J2                                 670                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J2                                 671                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J2                                 672                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J2                                 673                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J2                                 674                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J2                                 675                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J3                                 676                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J3                                 677                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J3                                 678                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J3                                 679                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J3                                 680                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J3                                 681                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J4                                 682                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J4                                 683                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J4                                 684                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J4                                 685                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J4                                 686                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J4                                 687                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CH.sub.3     J5                                 688                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 689                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           isopropyl    J5                                 690                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           t-butyl      J5                                 691                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J5                                 692                                                                              NH       CH      2-3 4-Cl, 6-F                                                                           CO.sub.2 CH.sub.3                                                                          J5                                 693                                                                              NCH.sub.3                                                                              CH      2-3 4-Cl, 6-F                                                                           CF.sub.3     J1                                 694                                                                              NH       CH      2-3 4-Cl  CF.sub.3     J1                                 695                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 696                                                                              CH       NCH.sub.2 C.sub.6 H.sub.5                                                             1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 697                                                                              CH       NCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                    1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 698                                                                              CH       NCOCH.sub.3                                                                           1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 699                                                                              CH       NCH.sub.2 C.tbd.N                                                                     1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 700                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CF.sub.3     J1                                 701                                                                              CH       NH      1-2 4-Cl, 6-F                                                                           CO.sub.2 C.sub.2 H.sub.5                                                                   J1                                 702                                                                              CH       NH      1-2 4-Cl  CO.sub.2 C.sub.2 H.sub.5                                                                   J1                                 703                                                                              N        O       1-2 4-Cl, 6-F                                                                           CH.sub.3     J7                                 704                                                                              O        CH      1-2 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J7                                 705                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J6                                 706                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.3                                                                          J6                                 707                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CF.sub.3     J7                                 708                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 C(CH.sub.3).sub.3                                                                 J1                                 709                                                                              NH       N       2-3 4-Cl, 6-F                                                                           3,5-dimethylisoxazolyl                                                                     J1                                 710                                                                              NH       N       2-3 4-Cl, 6-F                                                                           pyridin-2-yl J1                                 711                                                                              NCOCH.sub.3                                                                            N       2-3 4-Cl, 6-F                                                                           H            J1                                 712                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.7 F.sub.15                                                                           J1                                 713                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CHCl.sub.2   J1                                 714                                                                              NH       N       2-3 4-Cl, 6-F                                                                           NHCO.sub.2 C.sub.2 H.sub.5                                                                 J1                                 715                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)NHCH.sub.2 CO.sub.2 C.sub.2                                       H.sub.5      J1                                 716                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(CH.sub.3)OCOCH.sub.3                                                                    J1                                 717                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3)═CH.sub.2                                                                   J1                                 718                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH═C(CH.sub.3).sub.2                                                                   J1                                 719                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(Br)CH.sub.3                                                                             J1                                 720                                                                              NH       N       2-3 6-F   CF.sub.3     J1                                 721                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH═NC.sub.6 H.sub.5                                                                    J1                                 722                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 OCOCH.sub.3                                                                       J1                                 723                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(OCH.sub.3)C.sub.6 H.sub.5                                                               J1                                 724                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH(OCOCH.sub.3)C.sub.6 H.sub.5                                                             J1                                 725                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.3    J1                                 726                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.5                                                                            J5                                 727                                                                              NCH.sub.3                                                                              N       2-3 4,6-Cl.sub.2                                                                        CF.sub.3     J1                                 728                                                                              N        NCH.sub.3                                                                             2-3 4,6-Cl.sub.2                                                                        CF.sub.3     J1                                 729                                                                              NH       NH      --  4-Cl, 6-F                                                                           CF.sub.3     J1                                 730                                                                              NH       N       2-3 4,6-Cl.sub.2                                                                        CF.sub.3     J5                                 731                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SO.sub.2 CH.sub.3                                                                          J1                                 732                                                                              NH       N       2-3 4-Br, 6-F                                                                           CF.sub.3     J1                                 733                                                                              NH       N       2-3 4-Br, 6-F                                                                           C.sub.2 H.sub.5                                                                            J1                                 734                                                                              NH       N       2-3 4-Cl, 6-F                                                                           CH.sub.2 OH  J1                                 735                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 OH                                                                       J1                                 736                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3)OCH.sub.2 C.sub.6 H.sub.5                                                       J1                                 737                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SH           J1                                 738                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH(CH.sub.3)C.tbd.N                                                                       J1                                 739                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SC.sub.2 H.sub.5                                                                           J1                                 740                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C.tbd.CH                                                                         J1                                 741                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C.sub.6 H.sub.5                                                                  J1                                 742                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SC.tbd.N     J1                                 743                                                                              NH       N       2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 CH.sub.2 SC.tbd.N                                                        J1                                 744                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                                                      J1                                 745                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH(CH.sub.3)CON(CH.sub.3).sub.2                                                           J1                                 746                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C.tbd.CH                                                                         J5                                 747                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C═CH.sub.2                                                                   J1                                 748                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C.tbd.N                                                                          J1                                 749                                                                              NH       N       2-3 4-Cl, 6-F                                                                           SCH.sub.2 C.tbd.CCH.sub.2 Cl                                                               J1                                 750                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 OCONHCH.sub.3                                                                     J1                                 751                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 NHCOCH.sub.2 (C.sub.6 H.sub.4,                                                    J1                                                               2-NO.sub.2)  J1                                 752                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3)(OH)C.sub.6 H.sub.5                                                             J1                                 753                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 NH.sub.2                                                                          J1                                 754                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3)(OH)CH(CH.sub.3).sub.2                                                          J1                                 755                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 NHCOCH.sub.3                                                                      J1                                 756                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 NHSO.sub.2 CH.sub.3                                                               J1                                 757                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C(CH.sub.3).sub.2 F                                                                        J1                                 758                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CO.sub.2 H                                                                        J1                                 759                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CON(CH.sub.3).sub.2                                                               J1                                 760                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CON(CH.sub.3)(OCH.sub.3)                                                          J1                                 761                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CONHCH.sub.3                                                                      J1                                 762                                                                              O        CH      2-3 4-Cl, 6-F                                                                           CH.sub.2 CONH.sub.2                                                                        J1                                 763                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 CON(CH.sub.3)(OCH.sub.3)                                                   J1                                 764                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 CO.sub.2 CH.sub.3                                                          J1                                 765                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.3 H.sub.6 OH                                                                         J1                                 766                                                                              O        CH      2-3 4-Cl, 6-F                                                                           C.sub.2 H.sub.4 CONHCH.sub.3                                                               J1                                 767                                                                              NH       N       2-3 4-Cl  SCF.sub.3    J1                                 768                                                                              NH       N       2-3 4-Cl  CF.sub.3     J1                                 769                                                                              NH       N       2-3 4-Cl  CF.sub.3     J3                                 __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Characterizing Data                                                           Melting Points or Physical States of Representative Compounds                 No.                                                                              MP/State                                                                            No.                                                                              MP/State                                                                              No.                                                                              MP/State                                                                              No.                                                                              MP/State                                    __________________________________________________________________________     1 OIL   246                                                                              45-9    377                                                                              122-30  722                                                                              117-122 RESIN                                16                                                                              70-72 247                                                                              35-8    378                                                                              200 C>  723                                                                              107-112 RESIN                                25                                                                              OIL   248                                                                               67-71  379                                                                              116-22  724                                                                              108-114 RESIN                                26                                                                              OIL   249                                                                              84-9    380                                                                              201-4   725                                                                              135-140 RESIN                                28                                                                              OIL   250                                                                               65-68  381                                                                              117-24  726                                                                              >210                                         30                                                                              OIL   251                                                                              55-7    382                                                                              193-5   727                                                                              182-183                                      38                                                                              246-9 252                                                                              OIL     383                                                                              131-40  728                                                                              174-175                                      42                                                                              >250  253                                                                              GLASS   384                                                                              103-5   729                                                                              >205                                         43                                                                              SOLID 254                                                                              71-5    385                                                                              158-160 730                                                                              >205                                         49                                                                              OIL   255                                                                              134-8   386                                                                              132-5   731                                                                              150-152 RESIN                                96                                                                              OIL   256                                                                              145-7   387                                                                              112-4   732                                                                              195-200                                      98                                                                              >245  257                                                                              OIL     388                                                                              107-9   733                                                                              >205                                         99                                                                              OIL   258                                                                              232-40  399                                                                              177.5-8.5                                                                             734                                                                              SOLID                                       100                                                                              OIL   259                                                                              165-9   405                                                                                130   735                                                                              118-121 RESIN                               101                                                                              OIL   260                                                                              55-8    469                                                                               98-100 736                                                                              88-92                                       102                                                                              OIL   261                                                                              65-7    481                                                                              SOLID   737                                                                              >200                                        103                                                                              OIL   262                                                                              75-7    493                                                                              187-8   738                                                                              133-135                                     104                                                                              OIL   263                                                                              >50     500                                                                              208-10  739                                                                              130-132                                     105                                                                              >250  264                                                                              155-7   513                                                                              178-181 740                                                                              178-180                                     106                                                                              OIL   265                                                                              130-6   522                                                                              78-80   741                                                                              118-121 RESIN                               107                                                                              OIL   266                                                                              258-61  527                                                                              152-154 742                                                                              150-155                                     108                                                                              >250  267                                                                              110-8   563                                                                              165-166 743                                                                              SOLID                                       109                                                                              OIL   268                                                                              73-7    595                                                                              >240    744                                                                              160-162                                     110                                                                              OIL   269                                                                              270-5   618                                                                                235-237.5                                                                           745                                                                              >200                                        112                                                                              86-88 270                                                                              265-72  693                                                                              60-65   746                                                                              106-109                                     221                                                                              193.5-6                                                                             271                                                                               62-72  694                                                                              221.5-223                                                                             747                                                                               98-100                                     222                                                                              183-6 272                                                                              OIL     695                                                                              160-162 748                                                                              104-110 RESIN                               223                                                                              OIL   273                                                                               220-2.5                                                                              696                                                                              173-177 749                                                                              155-158 RESIN                               224                                                                              OIL   274                                                                              116 SOFTENS                                                                           697                                                                              60-63   750                                                                              137-139                                     225                                                                              OIL   275                                                                              OIL     698                                                                                142-145.5                                                                           751                                                                              189-190                                     226                                                                              63-6  276                                                                              145-53  699                                                                               95-102 752                                                                              78-82                                       227                                                                              134-6 277                                                                              179-82  700                                                                              160-162 753                                                                              87-89                                       228                                                                              42-5  278                                                                              189-92  701                                                                              245-248 754                                                                              75-77                                       229                                                                              OIL   279                                                                              197-8   702                                                                              258-260 755                                                                              96-98                                       230                                                                              163-5 280                                                                              215-6   705                                                                              102-103 756                                                                              90-92                                       231                                                                              65-70 362                                                                              152-8   706                                                                              88-89   757                                                                              60-62                                       232                                                                              186-91                                                                              363                                                                              >165    708                                                                              140 DEC 758                                                                              95-97                                       233                                                                              85-90 364                                                                              SOLID   709                                                                              >200    759                                                                              144-146                                     234                                                                              65-70 365                                                                              172-7   710                                                                              130 RESIN                                                                             760                                                                              146-147                                     235                                                                              63-7  366                                                                                130   711                                                                              >200    761                                                                              70-76                                       236                                                                              56-8  367                                                                              150-5   712                                                                              93-98 RESIN                                                                           762                                                                              185-187                                     237                                                                              141-2 368                                                                               87-93  713                                                                              123-130 RESIN                                                                         763                                                                              63-65                                       238                                                                              143-5 369                                                                              125-30  714                                                                              160-165 RESIN                                                                         754                                                                              OIL                                         239                                                                              162-4 370                                                                                130   715                                                                              90-95   765                                                                              50-54                                       240                                                                              72-6  371                                                                              SOLID   716                                                                              115-120 RESIN                                                                         766                                                                              172-173                                     241                                                                              67-70 372                                                                              SOLID   717                                                                              120-125 767                                                                              239-241                                     242                                                                              163-5 373                                                                                160   718                                                                              110-116                                                243                                                                              51-55 374                                                                                190   719                                                                              120-125                                                244                                                                              OIL   375                                                                              >200    720                                                                              128-132 RESIN                                          245                                                                              OIL   376                                                                              142-8   721                                                                              145-150                                                __________________________________________________________________________

Biological Testing

The benzofused heterocyclic compounds of this invention were tested forpre- and postemergence herbicidal activity using a variety of crops andweeds. The test plants included soybean (Glycine max var. Winchester),field corn (Zea mays var. Pioneer 3732), wheat (Triticum aestivum var.Lew), morningglory (Ipomea lacunosa or Ipomea hederacea), velvetleaf(Abutilon theophrasti), green foxtail (Setaria viridis), Johnsongrass(Sorghum halepense), blackgrass (Aloepecurus myosuroides), commonchickweed (Stellaria media), and common cocklebur (Xanthium strumariumL.).

For preemergence testing, two disposable fiber flats (8 cm×15 cm×25 cm)for each rate of application of each candidate herbicide were filled toan approximate depth of 6.5 cm with steam-sterilized sandy loam soil.The soil was leveled and impressed with a template to provide fiveevenly spaced furrows 13 cm long and 0.5 cm deep in each flat. Seeds ofsoybean, wheat, corn, green foxtail, and johnsongrass were planted inthe furrows of the first flat, and seeds of velvetleaf, morningglory,common chickweed, cocklebur, and blackgrass were planted in the furrowsof the second flat. The five-row template was employed to firmly pressthe seeds into place. A topping soil of equal portions of sand and sandyloam soil was placed uniformly on top of each flat to a depth ofapproximately 0.5 cm. Flats for postemergence testing were prepared inthe same manner except that they were planted 9-14 days prior to thepreemergence flats and were placed in a greenhouse and watered, thusallowing the seeds to germinate and the foliage to develop.

In both pre- and postemergence tests, a stock solution of the candidateherbicide was prepared by dissolving 0.27 g of the compound in 20 mL ofwater/acetone (50/50) containing 0.5% v/v sorbitan monolaurate. For anapplication rate of 3000 g/ha of herbicide a 10 mL portion of the stocksolution was diluted with water/acetone (50/50) to 45 mL. The volumes ofstock solution and diluent used to prepare solutions for lowerapplication rates are shown in the following table:

    ______________________________________                                        Application                                                                            Volume of  Volume of    Total, Volume                                Rate     Stock Solution                                                                           Acetone/Water                                                                              of Spray Solution                            (g/ha)   (mL)       (mL)         (mL)                                         ______________________________________                                        3000     10         35           45                                           1000     3          42           45                                            300     1          44           45                                            100     0.3        45           45.3                                          30      0.1        45           45.1                                          10      0.03       45           45.03                                          3      0.01       45           45.01                                        ______________________________________                                    

The preemergence flats were initially subjected to a light water spray.The four flats were placed two by two along a conveyor belt (i.e., thetwo preemergence followed by the two postemergence flats). The conveyorbelt fed under a spray nozzle mounted about ten inches above thepostemergent foliage. The preemergent flats were elevated on the belt sothat the soil surface was at the same level below the spray nozzle asthe foliage canopy of the postemergent plants. The spray of herbicidalsolution was commenced and once stabilized, the flats were passed underthe spray at a speed to receive a coverage equivalent of 1000 L/ha. Atthis coverage the application rates are those shown in the above tablefor the individual herbicidal solutions. The preemergence flats werewatered immediately thereafter, placed in the greenhouse and wateredregularly at the soil surface. The postemergence flats were immediatelyplaced in the green-house and not watered until 24 hours after treatmentwith the test solution. Thereafter they were regularly watered at groundlevel. After 12-17 days the plants were examined and the phytotoxicitydata were recorded.

Herbicidal activity data at selected application rates are given forvarious compounds of this invention in Table 4 and Table 5. The testcompounds are identified by numbers which correspond to those in Tables1 and 2.

Phytotoxicity data were taken as percent control. Percent control wasdetermined by a method similar to the 0 to 100 rating system disclosedin "Research Methods in Weed Science," 2nd ed., B. Truelove, Ed.;Southern Weed Science Society; Auburn University, Auburn, Ala., 1977.The rating system is as follows:

    ______________________________________                                        Herbicide Rating System                                                       Rating Description                                                            Percent                                                                              of Main    Crop          Weed                                          Control                                                                              Categories Description   Description                                   ______________________________________                                         0     No effect  No crop       No weed                                                         reduction/injury                                                                            control                                       10                Slight dis-   Very poor weed                                                  coloration or stunting                                                                      control                                       20     Slight     Some discoloration,                                                                         Poor weed                                            eftect     stunting or   control                                                         stand loss                                                  30                Crop injury   Poor to defi-                                                   more pronounced                                                                             cient weed                                                      but not lasting                                                                             control                                       40                Moderate injury,                                                                            Deficient weed                                                  crop usually recovers                                                                       control                                       50     Moderate   Crop injury   Deficient to                                         effect     more lasting, moderate weed                                                   recovery doubtful                                                                           control                                       60                Lasting crop  Moderate weed                                                   injury, no recovery                                                                         control                                       70                Heavy injury and                                                                            Control some-                                                   stand loss    what less than                                                  satisfactory                                                80     Severe     Crop nearly destroyed                                                                       Satisfactory to                                                 a few survivors                                                                             weed control                                  90                Only occasional                                                                             Very good to                                                    live plants left                                                                            excellent control                             100    Complete   Complete crop Complete weed                                        effect     destruction   destruction                                   ______________________________________                                    

Formulation

The compounds of the present invention were tested in the laboratory aswater/acetone (50/50) solutions containing 0.5% v/v sorbitan monolaurateemulsifier. It is expected that all formulations normally employed inapplications of herbicides would be usable with the compounds of thepresent invention. These include wettable powders, emulsifiableconcentrates, water suspensions, flowable concentrates, and the like.

                                      TABLE 4                                     __________________________________________________________________________    PREEMERGENCE HERBICIDAL ACTIVITY (% CONTROL)                                  No.                                                                              SOY                                                                              WHT                                                                              CRN                                                                              ABUTH                                                                              IPOSS                                                                             STEME                                                                             XANPE                                                                             ALOMY                                                                              SETVI                                                                             SORHA                                   __________________________________________________________________________     1 100                                                                               85                                                                               90                                                                              100  100 100 100  90  100  95                                      16                                                                              100                                                                               70                                                                               90                                                                              100  100 100  90  80  100  95                                      25                                                                              100                                                                              100                                                                              100                                                                              100  100 100  95  90  100 100                                      26                                                                              100                                                                               90                                                                               90                                                                              100  100 100 100  95  100 100                                      28                                                                              100                                                                              100                                                                               95                                                                              100  100 100 100 100  100 100                                      30                                                                              100                                                                              100                                                                               95                                                                              100  100 100  90 100  100 100                                      38                                                                               60                                                                               50                                                                               80                                                                              100  100  0   70  30   75  60                                      42                                                                               0  10                                                                               0 100   60  30  20  50   30  0                                       43                                                                               50                                                                               40                                                                               80                                                                              100  100  10 --   60   70  80                                      49                                                                               95                                                                               50                                                                               80                                                                              100  100  20  90 --   100  90                                      96                                                                              100                                                                               90                                                                               95                                                                              100  100 100 --   90  100  95                                      98                                                                               50                                                                               40                                                                               80                                                                               80   75  70  60  10   30  65                                      99                                                                               40                                                                               50                                                                               60                                                                              100  100 100 --   60  100  65                                     100                                                                               40                                                                               30                                                                               80                                                                              100  100  20 --   60   50  70                                     101                                                                               80                                                                               70                                                                              100                                                                              100  100 --   80  80  100 100                                     102                                                                               20                                                                               30                                                                               10                                                                              100   70 --   50  90  100  60                                     103                                                                               50                                                                               50                                                                               80                                                                              100  100 --   70  90  100  70                                     104                                                                              100                                                                              100                                                                              100                                                                              100  100 --  100 100  100 100                                     106                                                                               30                                                                               40                                                                               70                                                                              100  100  95  60  70   90   55                                    107                                                                               80                                                                               60                                                                               90                                                                              100  100 100  40  75  100 100                                     108                                                                               0  0  10                                                                               70   50  40  10  50   50  30                                     109                                                                              100                                                                              100                                                                               90                                                                              100  100 100 100 100  100 100                                     110                                                                              100                                                                               50                                                                               70                                                                              100   90 100  40  80  100 100                                     112                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     221                                                                               70                                                                               60                                                                               85                                                                              100  100  80 ND  ND   100  95                                     222                                                                              100                                                                               70                                                                               90                                                                              100  100 100 100 ND   100 100                                     223                                                                              100                                                                               50                                                                               80                                                                              100  100 100  90 ND   100 100                                     224                                                                              100                                                                               80                                                                               90                                                                              100  100 100  95  80  100 100                                     225                                                                               40                                                                               20                                                                               30                                                                               90   50  70  50 ND   100  60                                     226                                                                               70                                                                               50                                                                               70                                                                              100   90  90  60 ND   100  80                                     227                                                                              100                                                                               80                                                                               90                                                                              100  100 100 ND   95  100 100                                     228                                                                              100                                                                               80                                                                               95                                                                              100  100 100  90 ND   100 100                                     229                                                                              100                                                                               70                                                                               90                                                                              100  100 100  95  80  100 100                                     230                                                                              100                                                                               40                                                                               80                                                                              100  100 100 100  80  100 100                                     231                                                                              100                                                                               80                                                                              100                                                                              100  100 100 100  90  100 100                                     232                                                                               20                                                                               30                                                                               50                                                                               90   80  20  10 ND    40  25                                     233                                                                               40                                                                               30                                                                               70                                                                              100   95  20  20 ND    60  50                                     234                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100  80  100 100                                     235                                                                              100                                                                               90                                                                              100                                                                              100  100 100 100  80  100 100                                     236                                                                              100                                                                               70                                                                               95                                                                              100  100 100 100  80  100 100                                     237                                                                              100                                                                               90                                                                               90                                                                              100  100 100 100 100  100 100                                     238                                                                              100                                                                               60                                                                               70                                                                              100  100  60  80  50   90  90                                     239                                                                              100                                                                               70                                                                               90                                                                              100  100 100 ND  ND   100  90                                     240                                                                              100                                                                               95                                                                               95                                                                              100  100 100 100 ND   100 100                                     241                                                                               60                                                                               70                                                                               95                                                                              100  100 100 100 ND   100 100                                     242                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     243                                                                              100                                                                               80                                                                               95                                                                              100  100 100 100 ND   100 100                                     244                                                                               95                                                                               80                                                                              100                                                                              100   90  70 100  70  100 100                                     245                                                                              100                                                                               60                                                                               80                                                                              100  100  90 100  70  100  80                                     246                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     247                                                                              100                                                                               90                                                                               90                                                                              100  100  95 100  85  100 100                                     248                                                                              100                                                                               90                                                                               95                                                                              100  100 100 100  95  100 100                                     249                                                                              100                                                                               80                                                                               95                                                                              100  100 100  90  80   10 100                                     250                                                                               80                                                                               40                                                                               50                                                                              100  100 ND  100  60  100  70                                     251                                                                               90                                                                               90                                                                               95                                                                              100  100  95 100  90  100 100                                     252                                                                              100                                                                              100                                                                              100                                                                              100  100 100 ND  100  100 100                                     253                                                                              100                                                                              95 100                                                                              100  100 100 ND  ND   100 100                                     254                                                                               25                                                                               20                                                                               80                                                                              100   50  30  50  60  100  80                                     255                                                                              100                                                                               90                                                                               95                                                                              100  100 100 100 ND   100 100                                     256                                                                              100                                                                               80                                                                               95                                                                              100  100 100 ND   70  100  90                                     257                                                                               40                                                                               0  10                                                                               90   70  0   20  20   70  10                                     258                                                                               30                                                                               30                                                                               75                                                                              100   60  0   60 ND    40  40                                     259                                                                               70                                                                               40                                                                               80                                                                              100   70 100  55 ND   100  95                                     260                                                                              100                                                                               70                                                                               80                                                                              100  100 100 100  95  100 100                                     261                                                                              100                                                                               80                                                                               95                                                                              100  100 100  90  80  100 100                                     262                                                                               90                                                                               40                                                                               40                                                                              100  100 100 100  50  100  70                                     263                                                                              100                                                                               50                                                                               65                                                                              100  100 100  95  75  100  70                                     264                                                                               0  0  10                                                                               20   0   20  30  0    10  10                                     265                                                                               70                                                                               40                                                                               80                                                                               90  100  20  70 ND    80  60                                     266                                                                               50                                                                               30                                                                               60                                                                               40   70  0   0  ND    30  30                                     267                                                                               0  10                                                                               20                                                                               10   10  0   50  50   5   0                                      268                                                                               30                                                                               30                                                                               50                                                                              100   95  20  0  ND    60  60                                     269                                                                               60                                                                               30                                                                               80                                                                              100  100 100 100  70  100  75                                     270                                                                               70                                                                               70                                                                               90                                                                              100  100 ND   60  65  100 100                                     271                                                                               80                                                                               70                                                                               90                                                                              100  100 100 100  80  100  90                                     272                                                                               20                                                                               0  20                                                                              100   70 100  20  70   90  60                                     273                                                                              100                                                                               80                                                                               90                                                                              100  100 100 100  90  100 100                                     274                                                                              100                                                                              100                                                                               90                                                                              100  100  90 100  95  100 100                                     275                                                                              100                                                                               80                                                                              100                                                                              100  100 100 100  80  100  95                                     362                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     363                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     364                                                                              100                                                                               60                                                                               80                                                                              100  100 100 100  80  100  80                                     365                                                                              ND  30                                                                               30                                                                              100  100 100 100  60   75  60                                     366                                                                               10                                                                               10                                                                               0  70   20  0   10  0    50  40                                     367                                                                              100                                                                               95                                                                              100                                                                              100  100 100 100  90  100 100                                     368                                                                              100                                                                              100                                                                               95                                                                              100  100 100 100  95  100 100                                     369                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     370                                                                              100                                                                              100                                                                               95                                                                              100  100 100 100  90  100 100                                     371                                                                              100                                                                               95                                                                              100                                                                              100  100 100 100 100  100 100                                     372                                                                              100                                                                               90                                                                               95                                                                              100  100 100 100  80  100  80                                     373                                                                              100                                                                               70                                                                               90                                                                              100  100 100 100  70  100  90                                     374                                                                               30                                                                               0  10                                                                              100   95  90  80  40  100  75                                     375                                                                               80                                                                               30                                                                               90                                                                              100   80  95  80  80  100  95                                     376                                                                               50                                                                               60                                                                               80                                                                              100  100 100 100 100  100  70                                     377                                                                              100                                                                               70                                                                               90                                                                              100  100 ND  100 100  100 100                                     378                                                                               90                                                                               70                                                                               90                                                                              100  100 100 100  80  100  95                                     379                                                                              100                                                                               50                                                                               70                                                                              100  100 ND  100  80  100  95                                     380                                                                               80                                                                               35                                                                               20                                                                              100  100 ND   80  90  100  70                                     381                                                                              100                                                                               40                                                                               80                                                                              100  100 ND  100  90  100  80                                     382                                                                               60                                                                               45                                                                               30                                                                              100   70 ND   60  90   95  80                                     383                                                                               80                                                                               40                                                                               20                                                                              100   60 ND   70  80   75  55                                     399                                                                               95                                                                               80                                                                               95                                                                              100   95 100  70  60  100  0                                      493                                                                               80                                                                               70                                                                               90                                                                              100  100 100  70  75  100 100                                     500                                                                               95                                                                               75                                                                               90                                                                              100  100 100 100  75  100 100                                     522                                                                               90                                                                               40                                                                               80                                                                              100  100 100  50  75  100 100                                     595                                                                               10                                                                               0  0  60   50  10  20 ND    0   40                                     __________________________________________________________________________     Rate of Application is 0.3 Kg/Ha. SOY is soybean; WHT is wheat; CRN is        corn; ABUTH is velvetleaf; IPOSS is morningglory; STEME is chickweed;         XANPE is cocklebur; ALOMY is blackgrass, SETVI is green foxtail; SORHA is     johnsongrass                                                             

                                      TABLE 5                                     __________________________________________________________________________    POSTEMERGENCE HERBICIDAL ACTIVITY (% CONTROL)                                 No.                                                                              SOY                                                                              WHT                                                                              CRN                                                                              ABUTH                                                                              IPOSS                                                                             STEME                                                                             XANPE                                                                             ALOMY                                                                              SETVI                                                                             SORHA                                   __________________________________________________________________________     1  95                                                                               65                                                                               80                                                                              100  100  90 100  70   80  80                                      16                                                                               95                                                                               60                                                                               80                                                                              100  100  70  95  70   80  80                                      25                                                                              100                                                                               80                                                                               90                                                                              100  100 100 100  80  100  90                                      26                                                                              96  60                                                                               80                                                                              100  100  80 100  80  100  80                                      28                                                                              100                                                                               80                                                                               80                                                                              100  100 100  90 100  100  95                                      30                                                                               95                                                                               80                                                                               90                                                                              100  100 100 100  90  100 100                                      38                                                                               70                                                                               35                                                                               60                                                                              100  100  0   45  20   40  50                                      42                                                                               65                                                                               30                                                                               60                                                                               90   60 --   50  40  100  20                                      43                                                                               80                                                                               30                                                                               70                                                                              100  100  70  50 --    50  50                                      49                                                                               95                                                                               70                                                                               80                                                                              100  100  40  30 --   100  90                                      96                                                                              100                                                                               90                                                                               90                                                                              100  100 100 100 --   100 100                                      98                                                                               40                                                                               10                                                                               50                                                                               60   20  5   20  5    40  20                                      99                                                                               80                                                                               40                                                                               80                                                                              100  100  95  70 --    70  65                                     100                                                                               85                                                                               40                                                                               60                                                                               90  100  50  50 --    30  40                                     101                                                                               95                                                                               50                                                                               80                                                                              100  100 --  --   60   65  65                                     102                                                                               80                                                                               30                                                                               75                                                                              100  100 --  --   60   90  60                                     103                                                                               90                                                                               50                                                                               80                                                                              100   80 --   80  70  100  60                                     104                                                                              100                                                                              100                                                                              100                                                                              100  100 --  --  --   100 100                                     106                                                                               80                                                                               30                                                                               75                                                                              100  100 --  --   60  100  70                                     107                                                                               95                                                                               40                                                                              100                                                                              100  100 100 --   90  100 100                                     108                                                                               50                                                                               20                                                                               60                                                                               20   60  0   10  10   70  20                                     109                                                                               90                                                                               90                                                                               80                                                                              100  100 --  100  90  100  90                                     110                                                                               80                                                                               40                                                                               50                                                                              100  100 100  70  80   70                                         112                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     221                                                                               95                                                                               50                                                                               60                                                                              100  100 100  60  40   70  70                                     222                                                                              100                                                                               70                                                                               90                                                                              100  100 100 100 100  100 100                                     223                                                                               95                                                                               40                                                                               90                                                                              100  100 100 100 ND   100 100                                     224                                                                               95                                                                               70                                                                              100                                                                              100  100 100 100  90  100 ND                                      225                                                                               60                                                                               30                                                                               60                                                                              100   75 ND   70 ND    90  60                                     226                                                                               70                                                                               40                                                                               80                                                                              100   95  80  90 ND   100  80                                     227                                                                               95                                                                               60                                                                               90                                                                              100  100 100 100 100  100 100                                     228                                                                               90                                                                               50                                                                               80                                                                              100  100  80  95 ND   100  90                                     229                                                                               95                                                                               60                                                                               80                                                                              100  100 100 100  70  100 100                                     230                                                                               95                                                                               40                                                                               80                                                                              100  100  90 100  70  100  90                                     231                                                                              100                                                                               70                                                                              100                                                                              100  100 100 ND  100  100 100                                     232                                                                               75                                                                               50                                                                               30                                                                              100   80  20  40 ND    30  10                                     233                                                                               90                                                                               30                                                                               60                                                                              100  100  30  30 ND    30  30                                     234                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     235                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     236                                                                              100                                                                               75                                                                               90                                                                              100  100 100 100  80  100 100                                     237                                                                              100                                                                               95                                                                              100                                                                              100  100 ND  100 100  100 100                                     238                                                                               80                                                                               30                                                                               70                                                                              100  100 ND  100  40   80  70                                     239                                                                               95                                                                               60                                                                               80                                                                              100  100 100 100 ND   100  80                                     240                                                                               95                                                                               95                                                                              100                                                                              100  100 100 100 ND   100 100                                     241                                                                               90                                                                               60                                                                               70                                                                              100  100  85  95 ND   100  70                                     242                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     243                                                                               95                                                                               70                                                                               95                                                                              100  100 100 100 ND   100 100                                     244                                                                               95                                                                               60                                                                               90                                                                              100  100 100 100  75  100 ND                                      245                                                                               85                                                                               40                                                                               75                                                                              100  100  60  70  50   70  70                                     246                                                                               95                                                                              100                                                                              100                                                                              100  100 100 100 ND   100 100                                     247                                                                               95                                                                               80                                                                              100                                                                              100  100 100 100 100  100 ND                                      248                                                                               80                                                                               50                                                                               95                                                                              100  100 100 100 ND   100 100                                     249                                                                               95                                                                               80                                                                              100                                                                              100  100 100 100 100  100 ND                                      250                                                                               95                                                                               50                                                                               80                                                                              100  100  80 100  40  100 100                                     251                                                                               95                                                                               70                                                                               90                                                                              100  100 100  95 100  100  95                                     252                                                                               95                                                                               90                                                                              100                                                                              100  100 100 ND  100  100 100                                     253                                                                               95                                                                              100                                                                              100                                                                              100  100 100 100 ND   100 100                                     254                                                                               95                                                                               40                                                                               80                                                                              100   70 ND   95  50  100  80                                     255                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 ND   100 100                                     256                                                                              100                                                                               80                                                                               90                                                                              100  100 100 100  80  100 100                                     257                                                                               70                                                                               20                                                                               70                                                                              100   60  30  70  30   70  50                                     258                                                                               80                                                                               30                                                                               60                                                                               80   70  5   50  30   60  50                                     259                                                                               80                                                                               35                                                                               75                                                                              100   90  30  70  55   80  70                                     260                                                                               90                                                                               80                                                                               70                                                                              100  100 ND  100  90  100  90                                     261                                                                               95                                                                               80                                                                              100                                                                              100  100 100 100 100  100 100                                     262                                                                               95                                                                               60                                                                               80                                                                              100  100  95  95  50  100  80                                     263                                                                               95                                                                               80                                                                               90                                                                              100  100 100 100  60   90  70                                     264                                                                               50                                                                               20                                                                               50                                                                               40   40  0   30  0   ND   20                                     265                                                                               70                                                                               40                                                                               60                                                                              100  100  30  20 ND    40  20                                     266                                                                               60                                                                               40                                                                               60                                                                               50   60  10  10 ND    40  40                                     267                                                                               50                                                                               15                                                                               50                                                                               80   40  10  10  20   30  20                                     268                                                                               70                                                                               40                                                                               60                                                                               50   90  20 ND  ND    70  40                                     269                                                                               90                                                                               40                                                                               70                                                                              100   80  80 ND  ND    70  60                                     270                                                                               70                                                                               40                                                                               50                                                                              100   60  40 ND   50   50  50                                     271                                                                               80                                                                               40                                                                               60                                                                              100  100 100 ND  ND    70  50                                     272                                                                               50                                                                               30                                                                               45                                                                              100   60  50  50  20   70  40                                     273                                                                               95                                                                               60                                                                               95                                                                              100  100  90 100  80  100 100                                     274                                                                               95                                                                               60                                                                               95                                                                              100  100  90 100  90  100 100                                     275                                                                              100                                                                               70                                                                               90                                                                              100  100 100 100  95  100 100                                     362                                                                              100                                                                              100                                                                              100                                                                              100  100 100 ND  100  100 100                                     363                                                                              100                                                                              100                                                                              100                                                                              100  100 ND  100 100  100 100                                     364                                                                               95                                                                               40                                                                               80                                                                              100  100 100 100 ND   100 100                                     365                                                                              100                                                                               40                                                                               70                                                                              100  100 100 ND   70   80  30                                     366                                                                               70                                                                               30                                                                               80                                                                               95   80  30 100  30   50  50                                     367                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     368                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     369                                                                              100                                                                               80                                                                              100                                                                              100  100 ND  100 100  100 100                                     370                                                                              100                                                                               95                                                                              100                                                                              100  100 100 100 100  100 100                                     371                                                                               95                                                                              100                                                                              100                                                                              100  100 100 100 ND   100 100                                     372                                                                              100                                                                              100                                                                              100                                                                              100  100 100 100 100  100 100                                     373                                                                              100                                                                               80                                                                              100                                                                              100  100 100 100 100  100 100                                     374                                                                               80                                                                               25                                                                               30                                                                              100   95  80 100  25   80  60                                     375                                                                               95                                                                               40                                                                               90                                                                              100   95 100 100  90   80 100                                     376                                                                               90                                                                               50                                                                               95                                                                              100  100 ND  100  90  100 100                                     377                                                                               95                                                                               80                                                                              100                                                                              100  100 ND  100 100  100 100                                     378                                                                               90                                                                               40                                                                               90                                                                              100   90 ND  100  80  100 100                                     379                                                                               95                                                                               80                                                                              100                                                                              100  100 ND  100  70  100 100                                     380                                                                               95                                                                               30                                                                               95                                                                              100  100 ND  100  70  100  80                                     381                                                                               95                                                                               40                                                                               95                                                                              100  100 ND  100 100  100 100                                     382                                                                               80                                                                               40                                                                              100                                                                              100  100 ND  100  80   90  80                                     383                                                                               95                                                                               40                                                                               95                                                                              100   95 ND  100  60   95  70                                     399                                                                               95                                                                               30                                                                               70                                                                              100  100 100 100  50   70  60                                     493                                                                               95                                                                               60                                                                               90                                                                              100  100  80 100  65  100 100                                     500                                                                               95                                                                               65                                                                               95                                                                              100  100  90 100  80  100 100                                     522                                                                               90                                                                               45                                                                               90                                                                              100  100 100 100  50  100 100                                     595                                                                               50                                                                               10                                                                               60                                                                               30   40  0   20  10   20  20                                     __________________________________________________________________________     Rate of Application is 0.3 Kg/Ha. SOY is soybean; WHT is wheat; CRN is        corn; ABUTH is velvetleaf; IPOSS is morningglory; STEME is chickweed;         XANPE is cocklebur; ALOMY is blackgrass, SETVI is green foxtail; SORHA is     johnsongrass                                                             

Herbicidal compositions are prepared by combining herbicidally effectiveamounts of the active compounds with adjuvants and carriers normallyemployed in the art for facilitating the dispersion of activeingredients for the particular utility desired, recognizing the factthat the formulation and mode of application of a toxicant may affectthe activity of the material in a given application. Thus, foragricultural use the present herbicidal compounds may be formulated asgranules of relatively large particle size, as water-soluble orwater-dispersible granules, as powdery dusts, as wettable powders, asemulsifiable concentrates, as solutions, or as any of several otherknown types of formulations, depending on the desired mode ofapplication. It is to be understood that the amounts specified in thisspecification are intended to be approximate only, as if the word-about" were placed in front of the amounts specified.

These herbicidal compositions may be applied either as water-dilutedsprays, or dusts, or granules to the areas in which suppression ofvegetation is desired. These formulations may contain as little as 0.1%,0.2% or 0.5% to as much as 95% or more by weight of active ingredient.

Dusts are free flowing admixtures of the active ingredient with finelydivided solids such as talc, natural clays, kieselguhr, flours such aswalnut shell and cottonseed flours, and other organic and inorganicsolids which act as dispersants and carriers for the toxicant; thesefinely divided solids have an average particle size of less than about50 microns. A typical dust formulation useful herein is one containing1.0 part or less of the herbicidal compound and 99.0 parts of talc.

Wettable powders, also useful formulations for both pre- andpost-emergence herbicides, are in the form of finely divided particleswhich disperse readily in water or other dispersant. The wettable powderis ultimately applied to the soil either as a dry dust or as an emulsionin water or other liquid. Typical carriers for wettable powders includeFuller's earth, kaolin clays, silicas, and other highly absorbent,readily wet inorganic diluents. Wettable powders normally are preparedto contain about 5-80% of active ingredient, depending on the absorbencyof the carrier, and usually also contain a small amount of a wetting,dispersing or emulsifying agent to facilitate dispersion. For example, auseful wettable powder formulation contains 80.0 parts of the herbicidalcompound, 17.9 parts of Palmetto clay, and 1.0 part of sodiumlignosulfonate and 0.3 part of sulfonated aliphatic polyester as wettingagents. Additional wetting agent and/or oil will frequently be added tothe tank mix for post-emergence application to facilitate dispersion onthe foliage and absorption by the plant.

Other useful formulations for herbicidal applications are emulsifiableconcentrates (ECs) which are homogeneous liquid compositions dispersiblein water or other dispersant, and may consist entirely of the herbicidalcompound and a liquid or solid emulsifying agent, or may also contain aliquid carrier, such as xylene, heavy aromatic naphthas, isphorone, orother non-volatile organic solvents. For herbicidal application theseconcentrates are dispersed in water or other liquid carrier and normallyapplied as a spray to the area to be treated. The percentage by weightof the essential active ingredient may vary according to the manner inwhich the composition is to be applied, but in general comprises 0.5 to95% of active ingredient by weight of the herbicidal composition.

Flowable formulations are similar to ECs except that the activeingredient is suspended in a liquid carrier, generally water. Flowables,like ECs, may include a small amount of a surfactant, and will typicallycontain active ingredients in the range of 0.5 to 95%, frequently from10 to 50%, by weight of the composition. For application, flowables maybe diluted in water or other liquid vehicle, and are normally applied asa spray to the area to be treated.

Typical wetting, dispersing or emulsifying agents used in agriculturalformulations include, but are not limited to, the alkyl and alkylarylsulfonates and sulfates and their sodium salts; alkylaryl polyetheralcohols; sulfated higher alcohols; polyethylene oxides; sulfonatedanimal and vegetable oils; sulfonated petroleum oils; fatty acid estersof polyhydric alcohols and the ethylene oxide addition products of suchesters; and the addition product of long-chain mercaptans and ethyleneoxide. Many other types of useful surface-active agents are available incommerce. Surface-active agents, when used, normally comprise 1 to 15%by weight of the composition.

Other useful formulations include suspensions of the active ingredientin a relatively non-volatile solvent such as water, corn oil, kerosene,propylene glycol, or other suitable solvents.

Still other useful formulations for herbicidal applications includesimple solutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene, or other organic solvents. Granularformulations, wherein the toxicant is carried on relative coarseparticles, are of particular utility for aerial distribution or forpenetration of cover crop canopy. Pressurized sprays, typically aerosolswherein the active ingredient is dispersed in finely divided form as aresult of vaporization of a low boiling dispersant solvent carrier, suchas the Freon fluorinated hydrocarbons, may also be used. Water-solubleor water-dispersible granules are free-flowing, non-dusty, and readilywater-soluble or water-miscible. The soluble or dispersible granularformulations described in U.S. Pat. No. 3,920,442 are useful herein withthe present herbicidal compounds. In use by the farmer on the field, thegranular formulations, emulsifiable concentrates, flowable concentrates,solutions, etc., may be diluted with water to give a concentration ofactive ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%.

The active herbicidal compounds of this invention may be formulatedand/or applied with insecticides, fungicides, nematicides, plant growthregulators, fertilizers, or other agricultural chemicals and may be usedas effective soil sterilants as well as selective herbicides inagriculture. In applying an active compound of this invention, whetherformulated alone or with other agricultural chemicals, an effectiveamount and concentration of the active compound is of course employed;the amount may be as low as, e.g. about 1 to 250 g/ha, preferably about4 to 30 g/ha. For field use, where there are losses of herbicide, higherapplication rates (e.g., four times the rates mentioned above) may beemployed.

The active herbicidal compounds of the present invention may also beused in combination with other herbicides. Such herbicides include, forexample: N-(phosphonomethyl) glycine (--glyphosate"); aryloxyalkanoicacids such as (2,4-dichlorophenoxy)acetic acid (-2,4-D"),(4-chloro-2-methylphenoxy)acetic acid (--MCPA"),(+/-)-2-(4-chloro-2-methylphenoxy)propanoic acid (MCPP); ureas such asN,N-dimethyl-N'-[4-(1-methylethyl)phenyl]urea (-isoproturon");imidazolinones such as2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylicacid (-imazapyr"), a reaction product comprising(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4-methylbenzoicacid and(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methylbenzoicacid (-imazamethabenz"),(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylicacid (-imazethapyr"), and(+/-)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylicacid (-imazaquin"); diphenyl ethers such as5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid(-acifluorfen"), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate(-bifenox"), and5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide(-fomasafen"); hydroxy-benzonitriles such as4-hydroxy-3,5-diiodobenzonitrile (-ioxynil") and3,5-dibromo-4-hydroxybenzonitrile (-bromoxynil"); sulfonylureas such as2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoicacid (-chlorimuron"),2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide(-chlorsulfuron") , 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoicacid (-bensulfuron"),2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrazol-4-carboxylicacid (-pyrazosulfuron"),3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylicacid (-thifensulfuron"), and2-(2-chloroethoxy)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide(-triasulfuron"); 2-(4-aryloxyphenoxy)alkanoic acids such as(+/-)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propanoic acid(-fenoxaprop"),(+/-)-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid(-fluazifop"), (+/-)-2-[4-(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoicacid (-quizalofop"), and(+/-)-2-[-(2,4-dichlorophenoxy)phenoxy]propanoic acid (-diclofop");benzothiadiazinones such as3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide(-bentazone"); 2-chloroacetanilides such as N-butoxymethyl)-2-chloro-2',6'-diethylacetanilide (-butachlor");2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide(-metachlor"),2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide(-acetochlor"), and(RS)-2-chloro-N-(ethoxymethyl)-N-(2-methoxy-1-methylethyl)acetamide(-dimethenamide"); arenecarboxylic acids such as3,6-dichloro-2-methoxybenzoic acid (-dicamba"); and pyridyloxyaceticacids such as [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]aceticacid (-fluroxypyr").

It is apparent that various modifications may be made in theformulations and application of the compounds of the present inventionwithout departing from the inventive concepts herein, as defined in theclaims.

What is claimed is:
 1. A compound having the formula ##STR22## where Aand B are NH;R is hydrogen, hydroxy, mercapto, straight or branchedchain lower alkyl, cycloalkyl, alkoxy, aryl, heteroaryl, alkenyl,haloalkyl, hydroxyalkyl, haloaryl, alkoxyaryl, arylalkyl, aryloxyalkyl,haloarylalkyl, alkylthio, heterocyclyl, alkoxyalkyl,alkoxylalkyloxyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl,aminocarbonyloxyalkyl, aminoalkyl, cyanoalkyl, aminoalkenyl, carboxy,carboxyalkyl, alkylcarboxy, alkylcarboxyalkyl, formyl, aminocarbonyl,amino, oxygen, cyano, nitro, alkylsulfonyl, aminosulfonyl,alkylsulfonylamino, alkylcarboxyoxyalkyl, akylcarboxylalkoxy,alkoxycarbonylamino, alkoxycarbonylalkylaminoalkyl, aryliminoalkyl,(aryl)(alkoxy)alkyl, (aryl)(alkylcarbonyloxy)alkyl, arylalkoxyalkyl,cyanoalkylthio, alkynylalkylthio, arylalkylthio, cyanothio,cyanothioalkyl, alkoxycarbonylalkylthio, aminocarbonylalkylthio,alkenylalkylthio, haloalkylalkynylalkylthio, alkylcarbonylaminoalkyl,arylalkylcarbonylaminoalkyl, (hydroxy)(aryl)alkyl,alkylcarbonylaminoalkyl, alkylsulfonylaminoalkyl, aminocarbonylalkyl,alkoxycarbonyl, and alkenyloxy, where the amino group may be substitutedwith one or two substituents independently selected from alkyl, hydroxy,alkoxy, carboxy, aryl, alkylsufonyl or haloalkylsulfonyl; X is hydrogen,F, Cl, Br, alkyl, haloalkyl, CN, NO₂, or NH₂ ; n is 0-3; ##STR23## andR³ is hydrogen, alkyl, haloalkyl, CH₂ CN, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂CO₂ (alkyl), CH₂ OCH₃, or NH₂.
 2. A herbicidal composition comprising aherbicidally effective amount of a compound of claim 1 and aherbicidally compatible carrier therefor.
 3. A herbicidal compositioncomprising an herbicidally effective amount of a compound of claim 1 andan herbicidally effective amount of one or more herbicides selected fromthe group consisting of glyphosate, 2,4-D, MCPA, MCPP, isoproturon,imazapyr, imazamethabenz, imazethapyr, imazaquin, acifluorfen, bifenox,fomasafen, ioxynil, bromoxynil, chlorimuron, chlorsulfuron, bensulfuron,pyrazosulfuron, thifensulfuron, triasulfuron, fenoxaprop, fluazifop,quizalofop, diclofop, bentazone, butachlor, metachlor, acetochlor,dimethenamide, dicamba, and fluroxypyr.
 4. The herbicidal composition ofclaim 3 further comprising a herbicidally compatible carrier therefor.5. A method of controlling undesired plant growth, comprisingapplication to the locus where the undesired plants are growing or areexpected to grow, an herbicidally effective amount of a composition ofclaim
 3. 6. A method of controlling undesired plant growth, comprisingapplication to the locus where the undesired plants are growing or areexpected to grow, an herbicidally effective amount of a compound ofclaim
 1. 7. A compound having the formula ##STR24## where A is NH and Bis nitrogen double-bonded to position 2; R is hydrogen, hydroxy,mercapto, straight or branched chain lower alkyl, cycloalkyl, alkoxy,aryl, heteroaryl, alkenyl, haloalkyl, hydroxyalkyl, haloaryl,alkoxyaryl, arylalkyl, aryloxyalkyl, haloarylalkyl, alkylthio,heterocyclyl, alkoxyalkyl, alkoxylalkyloxyalkyl, alkylcarbonyloxyalkyl,arylcarbonyloxyalkyl, aminocarbonyloxyalkyl, aminoalkyl, cyanoalkyl,aminoalkenyl, carboxy, carboxyalkyl, alkylcarboxy, alkylcarboxyalkyl,formyl, aminocarbonyl, amino, oxygen, cyano, nitro, alkylsulfonyl,aminosulfonyl, alkylsulfonylamino, alkylcarboxyoxyalkyl,akylcarboxylalkoxy, alkoxycarbonylamino, alkoxycarbonylalkylaminoalkyl,aryliminoalkyl, (aryl)(alkoxy)alkyl, (aryl)(alkylcarbonyloxy)alkyl,arylalkoxyalkyl, cyanoalkylthio, alkynylalkylthio, arylalkylthio,cyanothio, cyanothioalkyl, alkoxycarbonylalkylthio,aminocarbonylalkylthio, alkenylalkylthio, haloalkylalkynylalkylthio,alkylcarbonylaminoalkyl, arylalkylcarbonylaminoalkyl,(hydroxy)(aryl)alkyl, alkylcarbonylaminoalkyl, alkylsulfonylaminoalkyl,aminocarbonylalkyl, alkoxycarbonyl, and alkenyloxy, where the aminogroup may be substituted with one or two substituents independentlyselected from alkyl, hydroxy, alkoxy, carboxy, aryl, alkylsufonyl orhaloalkylsulfonyl;X is F, Cl, Br, alkyl, haloalkyl, CN, NO₂, or NH₂ ; nis 2or 3; J is ##STR25## and R³ is hydrogen, alkyl, haloalkyl, CH₂ CN,CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ CO₂ (alkyl), CH₂ OCH₃, or NH₂.
 8. Thecompound of claim 1, wherein one X is attached at position
 4. 9. Thecompound of claim 1, wherein R is haloalkyl, X is F or Cl, n is 2, andR³ is alkyl.
 10. The compound of claim 9, wherein R is trifluoromethyl,X is F at position 6 and Cl at position 4, and R³ is methyl.
 11. Aherbicidal composition comprising a herbicidally effective amount of thecompound of claim 1 and a herbicidally compatible carrier therefore. 12.A herbicidal composition comprising a herbicidally effective amount ofthe compound of claim 1 and a herbicidally effective amount of one ormore herbicides selected from the group consisting of glyphosate, 2,4-D,MCPA, MCPP, isoproturon, imazapyr, imazamethabenz, imazethapyr,imazaquin, acifluorfen, bifenox, fomasafen, ioxynil, bromoxynil,chlorimuron, chlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron,triasulfuron, fenoxaprop, fluazifop, quizalofop, diclofop, bentazone,butachlor, dicamba, and fluroxypyr.
 13. The herbicidal composition ofclaim 12 further comprising a herbicidally compatible carrier therefor.14. A method of controlling undesired plant growth, comprisingapplication to the locus where the undesired plants are growing or areexpected to grow, a herbicidally effective amount of the composition ofclaim
 12. 15. A method of controlling undesired plant growth, comprisingapplication to the locus where the undesired plants are growing or areexpected to grow, a herbicidally effective amount of the compound ofclaim
 12. 16. A herbicidal composition comprising a herbicidallyeffective amount of the compound of claim 10 and a herbicidallycompatible carrier therefore.
 17. A herbicidal composition comprising aherbicidally effective amount of the compound of claim 10 and aherbicidally effective amount of one or more herbicides selected fromthe group consisting of glyphosate, 2,4-D, MCPA, MCPP, isoproturon,imazapyr, imazamethabenz, imazethapyr, imazaquin, acifluorfen, bifenox,fomasafen, ioxynil, bromoxynil, chlorimuron, chlorsulfuron, bensulfuron,pyrazosulfuron, thifensulfuron, triasulfuron, fenoxaprop, fluazifop,quizalofop, diclofop, bentazone, butachlor, dicamba, and fluroxypyr. 18.The herbicidal composition of claim 17 further comprising a herbicidallycompatible carrier therefor.
 19. A method of controlling undesired plantgrowth, comprising application to the locus where the undesired plantsare growing or are expected to grow, a herbicidally effective amount ofthe composition of claim
 17. 20. A method of controlling undesired plantgrowth, comprising application to the locus where the undesired plantsare growing or are expected to grow, a herbicidally effective amount ofthe compound of claim 10.